Pyrimidine derivatives and their use for controlling undesired plant growth

ABSTRACT

Pyrimidine derivatives and their use for controlling undesired plant growth Compounds of the formula (I) 
     
       
         
         
             
             
         
       
     
     and their use in the field of crop protection are described.

The invention relates to the technical field of crop protectioncompositions, in particular to that of the herbicides for the selectivecontrol of weeds and weed grasses in crops of useful plants.

Specifically, it relates to 2-aminopyrimidines, to processes for theirpreparation and to their use for controlling harmful plants.

The prior art discloses pyrimidines which have a herbicidal effect.Thus, for example, EP 0 523 533 A1 describes substituted4-aminopyrimidines and their use in the field of crop protection. WO2008/043031 discloses(R)-6-chloro-N⁴-fluorochroman-4-yl)pyrimidine-2,4,5-triamine as anintermediate for the preparation of pharmaceutically active purines.

However, the use of the derivatives of this type as selective herbicidesfor controlling harmful plants or as plant growth regulators in variouscrops of useful plants often requires an excessive application rate orleads to undesired damage to the useful plants. Moreover, the use of theactive ingredients is in many cases uneconomical on account ofrelatively high production costs.

It is therefore desirable to provide alternative chemical activeingredients based on pyrimidine derivatives which can be used asherbicides or plant growth regulators and with which certain advantagescompared to systems known from the prior art are associated.

Consequently, in general, the object of the present invention is toprovide alternative pyrimidine derivatives which can be used asherbicides or plant growth regulators, in particular with a satisfactoryherbicidal effect against harmful plants, with a broad spectrum againstharmful plants and/or with a high selectivity in crops of useful plants.These pyrimidine derivatives should here preferably exhibit a betterprofile of properties, in particular a better herbicidal effect againstharmful plants, a broader spectrum in respect of harmful plants and/or ahigher selectivity in crops of useful plants, than the pyrimidinederivatives known from the prior art.

According to the invention, then, novel pyrimidines have been foundwhich can be used advantageously as herbicides and plant growthregulators. Besides a good activity profile and crop plantcompatibility, the compounds of this series are characterized bycost-effective preparation processes and access options since thesubstances according to the invention can be prepared from inexpensiveand readily accessible precursors and it is therefore possible todispense with the use of costly and poor-availability intermediates.

Consequently, the present invention provides compounds of the formula(I) and their salts

in which

-   -   R¹ and R², independently of one another, are selected from the        group consisting of        -   hydrogen, halogen, hydroxy, cyano, nitro, amino, C(O)OH,            C(O)NH₂;        -   (C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl, (C₁-C₆)-alkylcarbonyl,            (C₁-C₆)-halo-alkylcarbonyl, (C₁-C₆)-alkylcarbonyloxy,            (C₁-C₆)-haloalkylcarbonyloxy,            (C₁-C₆)-alkylcarbonyl-(C₁-C₄)-alkyl;        -   (C₁-C₆)-alkoxy, (C₁-C₆)-haloalkoxy, (C₁-C₆)-alkoxycarbonyl,            (C₁-C₆)-haloalkoxycarbonyl,            (C₁-C₆)-alkoxycarbonyl-(C₁-C₆)-alkyl,            (C₁-C₆)-halo-alkoxycarbonyl-(C₁-C₆)-alkyl,            (C₁-C₆)-alkoxycarbonyl-(C₁-C₆)-haloalkyl,            (C₁-C₆)-haloalkoxycarbonyl-(C₁-C₆)-haloalkyl;        -   (C₂-C₆)-alkenyl, (C₂-C₆)-haloalkenyl,            (C₂-C₆)-alkenylcarbonyl, (C₂-C₆)-haloalkenylcarbonyl,            (C₂-C₆)-alkenyloxy, (C₂-C₆)-haloalkenyloxy,            (C₂-C₆)-alkenyloxycarbonyl, (C₂-C₆)-haloalkenyloxycarbonyl;        -   (C₂-C₆)-alkynyl, (C₂-C₆)-haloalkynyl,            (C₂-C₆)-alkynylcarbonyl, (C₂-C₆)-haloalkynylcarbonyl,            (C₂-C₆)-alkynyloxy, (C₂-C₆)-haloalkynyloxy,            (C₂-C₆)-alkynyloxycarbonyl, (C₂-C₆)-haloalkynyloxycarbonyl;        -   tri(C₁-C₆)-alkylsilyl-(C₂-C₆)-alkynyl,            di(C₁-C₆)-alkylsilyl-(C₂-C₆)-alkynyl,            mono(C₁-C₆)-alkylsilyl-(C₂-C₆)-alkynyl,            phenylsilyl-(C₂-C₆)-alkynyl;        -   (C₆-C₁₄)-aryl, (C₆-C₁₄)-aryloxy, (C₆-C₁₄)-arylcarbonyl and            (C₆-C₁₄)-aryl-oxycarbonyl, which may in each case be            substituted on the aryl moiety by halogen, (C₁-C₆)-alkyl            and/or (C₁-C₆)-haloalkyl;        -   (C₆-C₁₄)-aryl-(C₁-C₆)-alkyl, (C₆-C₁₄)-aryl-(C₁-C₆)-alkoxy,            (C₆-C₁₄)-aryl-(C₁-C₆)-alkylcarbonyl,            (C₆-C₁₄)-aryl-(C₁-C₆)-alkylcarbonyloxy,            (C₆-C₁₄)-aryl-(C₁-C₆)-alkoxycarbonyl,            (C₆-C₁₄)-aryl-(C₁-C₆)-alkoxycarbonyloxy;        -   mono((C₁-C₆)-alkyl)amino, mono((C₁-C₆)-haloalkyl)amino,            di((C₁-C₆)-alkyl)amino, di((C₁-C₆)-haloalkyl)amino,            ((C₁-C₆)-alkyl-(C₁-C₆)-haloalkyl)amino,            N—((C₁-C₆)-alkanoyl)amino, N—((C₁-C₆)-haloalkanoyl)-amino,            aminocarbonyl-(C₁-C₆)-alkyl,            di(C₁-C₆)-alkylaminocarbonyl-(C₁-C₆)-alkyl;        -   mono((C₁-C₆)-alkyl)aminocarbonyl,            mono((C₁-C₆)-haloalkyl)amino-carbonyl,            di((C₁-C₆)-alkyl)aminocarbonyl,            di((C₁-C₆)-haloalkyl)amino-carbonyl,            ((C₁-C₆)-alkyl-(C₁-C₆)-haloalkyl)aminocarbonyl,            N—((C₁-C₆)-alkanoyl)aminocarbonyl,            N—((C₁-C₆)-haloalkanoyl)aminocarbonyl;        -   (C₁-C₆)-alkoxy-(C₁-C₆)-alkyl, (C₁-C₆)-alkoxy-(C₁-C₆)-alkoxy,            (C₁-C₆)-alkoxycarbonyl-(C₁-C₆)-alkoxy;        -   (C₃-C₈)-cycloalkyl, which may be optionally substituted on            the cycloalkyl radical by (C₁-C₆)-alkyl and/or halogen;            (C₃-C₈)-cycloalkoxy, (C₃-C₈)-cycloalkyl-(C₁-C₆)-alkyl,            (C₃-C₈)-cycloalkyl-(C₁-C₆)-haloalkyl,            (C₃-C₈)-cycloalkyl-(C₁-C₆)-alkoxy,            (C₃-C₈)-cycloalkyl-(C₁-C₆)-haloalkoxy,            (C₃-C₈)-cycloalkylcarbonyl, (C₃-C₈)-cycloalkoxycarbonyl,            (C₃-C₈)-cycloalkyl-(C₁-C₆)-alkylcarbonyl,            (C₃-C₈)-cycloalkyl-(C₁-C₆)-haloalkylcarbonyl,            (C₃-C₈)-cycloalkyl-(C₁-C₆)-alkoxycarbonyl,            (C₃-C₈)-cycloalkyl-(C₁-C₆)-haloalkoxycarbonyl,            (C₃-C₈)-cycloalkylcarbonyloxy,            (C₃-C₈)-cycloalkoxycarbonyloxy,            (C₃-C₈)-cycloalkyl-(C₁-C₆)-alkylcarbonyloxy,            (C₃-C₈)-cycloalkyl-(C₁-C₆)-haloalkylcarbonyloxy,            (C₃-C₈)-cycloalkyl-(C₁-C₆)-alkoxycarbonyloxy,            (C₃-C₈)-cycloalkyl-(C₁-C₆)-haloalkoxycarbonyloxy;        -   (C₃-C₈)-cycloalkenyl, (C₃-C₈)-cycloalkenyloxy,            (C₃-C₈)-cycloalkenyl-(C₁-C₆)-alkyl,            (C₃-C₈)-cycloalkenyl-(C₁-C₆)-haloalkyl,            (C₃-C₈)-cycloalkenyl-(C₁-C₆)-alkoxy,            (C₃-C₈)-cycloalkenyl-(C₁-C₆)-haloalkoxy,            (C₃-C₈)-cycloalkenylcarbonyl,            (C₃-C₈)-cycloalkenyloxycarbonyl,            (C₃-C₈)-cycloalkenyl-(C₁-C₆)-alkylcarbonyl,            (C₃-C₈)-cycloalkenyl-(C₁-C₆)-haloalkylcarbonyl,            (C₃-C₈)-cycloalkenyl-(C₁-C₆)-alkoxycarbonyl,            (C₃-C₈)-cycloalkenyl-(C₁-C₆)-haloalkoxycarbonyl,            (C₃-C₈)-cycloalkenyl-carbonyloxy,            (C₃-C₈)-cycloalkenyloxycarbonyloxy,            (C₃-C₈)-cycloalkenyl-(C₁-C₆)-alkylcarbonyloxy,            (C₃-C₈)-cycloalkenyl-(C₁-C₆)-haloalkylcarbonyloxy,            (C₃-C₈)-cycloalkenyl-(C₁-C₆)-alkoxycarbonyloxy,            (C₃-C₈)-cycloalkenyl-(C₁-C₆)-haloalkoxycarbonyloxy;        -   hydroxy-(C₁-C₆)-alkyl, hydroxy-(C₁-C₆)-alkoxy,            cyano-(C₁-C₆)-alkoxy, cyano-(C₁-C₆)-alkyl;        -   (C₁-C₆)-alkylsulfonyl, (C₁-C₆)-alkylthio,            (C₁-C₆)-alkylsulfinyl, (C₁-C₆)-haloalkylsulfonyl,            (C₁-C₆)-haloalkylthio, (C₁-C₆)-haloalkylsulfinyl,            (C₁-C₆)-alkylsulfonyl-(C₁-C₆)-alkyl,            (C₁-C₆)-alkylthio-(C₁-C₆)-alkyl,            (C₁-C₆)-alkylsulfinyl-(C₁-C₆)-alkyl,            (C₁-C₆)-haloalkylsulfonyl-(C₁-C₆)-alkyl,            (C₁-C₆)-haloalkylthio-(C₁-C₆)-alkyl,            (C₁-C₆)-haloalkylsulfinyl-(C₁-C₆)-alkyl,            (C₁-C₆)-alkylsulfonyl-(C₁-C₆)-haloalkyl,            (C₁-C₆)-alkylthio-(C₁-C₆)-halo-alkyl,            (C₁-C₆)-alkylsulfinyl-(C₁-C₆)-haloalkyl,            (C₁-C₆)-haloalkylsulfonyl-(C₁-C₆)-haloalkyl,            (C₁-C₆)-haloalkylthio-(C₁-C₆)-haloalkyl,            (C₁-C₆)-haloalkylsulfinyl-(C₁-C₆)-haloalkyl,            (C₁-C₆)-alkylsulfonyloxy, (C₁-C₆)-haloalkylsulfonyloxy,            (C₁-C₆)-alkylthiocarbonyl, (C₁-C₆)-haloalkylthiocarbonyl,            (C₁-C₆)-alkylthiocarbonyloxy,            (C₁-C₆)-haloalkyl-thiocarbonyloxy,            (C₁-C₆)-alkylthio-(C₁-C₆)-alkyl,            (C₁-C₆)-alkylthio-(C₁-C₆)-alkoxy,            (C₁-C₆)-alkylthio-(C₁-C₆)-alkylcarbonyl,            (C₁-C₆)-alkylthio-(C₁-C₆)-alkylcarbonyloxy,            (C₄-C₁₄)-arylsulfonyl, (C₆-C₁₄)-arylthio,            (C₆-C₁₄)-arylsulfinyl, (C₃-C₈)-cycloalkylthio,            (C₃-C₈)-alkenylthio, (C₃-C₈)-cycloalkenylthio,            (C₃-C₆)-alkynylthio;        -   the radicals R¹ and R² together form a (C₂-C₆)-alkylene            group, which may comprise one or more oxygen and/or sulfur            atoms, where the (C₂-C₆)-alkylene group may be mono- or            polysubstituted by halogen and the respective halogen            substituents may be identical or different;    -   R³ is selected from the group consisting of hydrogen,        (C₁-C₆)-alkyl and (C₁-C₆)-haloalkyl;    -   R⁴ and    -   R⁵ in each case independently of one another are selected from        the group consisting of hydrogen, (C₁-C₆)-alkyl,        (C₁-C₆)-haloalkyl, hydroxy, (C₁-C₆)-alkoxy and        (C₁-C₆)-haloalkoxy; or, together with the carbon atom to which        they are bonded, form a three- to seven-membered ring;    -   R⁶ and    -   R⁷ in each case independently of one another are selected from        the group consisting of hydrogen, (C₁-C₆)-alkyl,        (C₁-C₆)-haloalkyl, (C₁-C₆)-alkoxy, (C₁-C₆)-haloalkoxy,        (C₆-C₁₄)-aryl, (C₆-C₁₄)-aryloxy, (C₆-C₁₄)-arylcarbonyl and        (C₆-C₁₄)-aryloxycarbonyl; or the radicals R⁶ and R⁷ together        form a (C₂-C₇)-alkylene group, which may comprise one or more        oxygen and/or sulfur atoms, where the (C₂-C₇)-alkylene group may        be mono- or polysubstituted by halogen and the respective        halogen substituents may be identical or different,    -   R⁸, R⁹, R¹⁰ and R¹¹, independently of one another, are in each        case selected from the group consisting of hydrogen, halogen,        cyano, nitro, (C₁-C₆)-alkyl, (C₁-C₆)-alkylcarbonyl,        (C₁-C₆)-alkyloxycarbonyl, (C₁-C₆)-alkylaminocarbonyl,        (C₁-C₆)-dialkylaminocarbonyl, (C₁-C₆)-haloalkyl, (C₁-C₆)-alkoxy,        (C₁-C₆)-haloalkoxy, (C₂-C₆)-alkynyl, (C₂-C₆)-haloalkynyl,        (C₂-C₆)-alkynylcarbonyl, (C₂-C₆)-haloalkynylcarbonyl,        (C₂-C₆)-alkynyloxy, (C₂-C₆)-haloalkynyloxy,        (C₂-C₆)-alkynyloxycarbonyl and (C₂-C₆)-haloalkynyloxycarbonyl;        and    -   X is a bond, CH₂, O, S, carbonyl, NH, CR¹²R¹³ and NR¹⁴,    -   R¹² and    -   R¹³ in each case independently of one another are selected from        the group consisting of hydrogen, (C₁-C₆)-alkyl and        (C₁-C₆)-haloalkyl,    -   R¹⁴ is selected from the group consisting of hydrogen,        (C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl,    -   provided    -   a) at least one radical of R¹, R⁴, R⁵, R⁶, R⁷, R⁸, R⁹, R¹⁰ or        R¹¹ is not hydrogen if R² is CF₃,    -   b) R² does not denote chloro if R¹ is NH₂.

The compounds according to the invention differ from the compoundsaccording to EP 0 523 533 A1 in that they are bicyclically substituted4-aminopyrimidine-2-amines.

According to the invention, it has been found that these compounds havea good activity profile and crop plant compatibility.

Now, firstly preferred, particularly preferred and very particularlypreferred meanings for the individual substituents are described below.

A first embodiment of the present invention encompasses compounds of theformula (I) in which

-   -   R¹ is preferably selected from the group consisting of hydrogen,        halogen, cyano, C(═O)NH₂, NO₂, (C₁-C₆)-alkyl,        (C₁-C₆)-alkylcarbonyl, (C₁-C₆)-haloalkyl, (C₃-C₆)-cyclopropyl,        (C₁-C₆)-alkoxy, (C₁-C₆)-thioalkyl, (C₂-C₆)-alkynyl,        mono(C₁-C₆)-alkylamino, di(C₁-C₆)-alkylamino and        tri(C₁-C₆)-alkyl-silyl-(C₂-C₆)-alkynyl;    -   R¹ is particularly preferably selected from the group consisting        of hydrogen, cyano, fluorine, chlorine, bromine, iodine, nitro,        trimethylsilylethynyl, methyl, ethyl, propyl, isopropyl, butyl,        tert-butyl, n-pentyl, n-heptyl, cyclopropyl, cyclobutyl, acetyl,        ethynyl, amino, dimethylamino, trifluoromethyl, difluoromethyl,        monofluoromethyl, methoxy, ethoxy and methoxymethyl; and    -   R¹ is very particularly preferably cyano, acetyl or        trifluoromethyl.

A second embodiment of the present invention encompasses compounds ofthe formula (I) in which

-   -   R² is preferably selected from the group consisting of hydrogen,        halogen, (C₁-C₆)-alkylphenyl; (C₆-C₁₄)-aryl, which may be        substituted on the aryl radical by (C₁-C₆)-alkyl,        (C₆-C₁₄)-haloalkyl and/or halogen; C₆-aryl-(C₁-C₆)-haloalkyl,        (C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl, (C₁-C₆)-alkoxy,        (C₁-C₆)-alkoxy-(C₁-C₆)-alkyl; (C₃-C₆)-cycloalkyl, which may be        substituted on the cycloalkyl radical by (C₁-C₆)-alkyl,        (C₆-C₁₄)-haloaryl and/or halogen; 1-(C₁-C₆)-alkylcyclopropyl,        1-((C₁-C₆)-alkyl-C₆-aryl)cyclopropyl,        1-(monohalophenyl)cyclopropyl, 1-(dihalophenyl)cyclopropyl,        mono(C₁-C₆)-alkylamino, di(C₁-C₆)-alkylamino, (C₁-C₆)-thioalkyl,        (C₁-C₆)-alkylthio, (C₁-C₆)-alkoxy and amino;    -   R² is particularly preferably selected from the group consisting        of hydrogen, chlorine, phenyl, 2-methylphenyl,        3-trifluoromethylphenyl, methyl, ethyl, isopropyl, butyl,        tert-butyl, n-pentyl, n-heptyl, trifluoromethyl,        1-methylcyclopropyl, 1-(p-xylyl)cyclopropyl,        1-(2,4-dichlorophenyl)cyclopropyl, amino, dimethylamino,        trifluoromethyl, difluoromethyl, monofluoromethyl, CHFCH₃,        CF(CH₃)₂, CHF(CH₂CH₃), 1-fluorocyclopropyl, cyclopentyl,        methoxy, ethoxy, methoxymethyl, ethoxymethyl, thiomethyl,        methylthio and methoxy; and    -   R² is very particularly preferably hydrogen, methyl or        difluoromethyl.

A third embodiment of the present invention encompasses compounds of theformula (I) in which

-   -   R¹ and R², preferably together with the carbon atoms to which        they are bonded, form a five- or six-membered ring, which may be        interrupted by one or two heteroatoms selected from the group        consisting of oxygen and sulfur;        -   particularly preferably together with the carbon atoms to            which they are bonded, form a five-membered ring, which may            be interrupted by a heteroatom selected from the group            consisting of oxygen and sulfur; and        -   are very particularly preferably —CH₂—CH₂—CH₂— or            —CH₂—S—CH₂—.

A fourth embodiment of the present invention encompasses compounds ofthe formula (I) in which

-   -   R³ is preferably hydrogen or (C₁-C₆)-alkyl; and    -   R³ is particularly preferably hydrogen.

A fifth embodiment of the present invention encompasses compounds of theformula (I) in which

-   -   R⁴ and R⁵, in each case independently of one another, are        preferably selected from the group consisting of hydrogen,        (C₁-C₆)-alkyl, hydroxy, cyclopropyl and (C₁-C₆)-alkoxy;    -   R⁴ and R⁵, in each case independently of one another, are        particularly preferably selected from the group consisting of        hydrogen, methyl, ethyl, propyl, cyclopropyl, hydroxy and        methoxy; and    -   R⁴ and R⁵, in each case independently of one another, are very        particularly preferably methyl, ethyl or hydrogen.

In this fifth embodiment, it is specifically preferred if at least oneof the radicals R⁴ or R⁵ is hydrogen. It is further preferred if atleast one of the radicals R⁴ or R⁵ is hydrogen and the other radical R⁴or R⁵ is not hydrogen, in particular (C₁-C₆)-alkyl.

In this fifth embodiment, it is very specifically preferred if one ofthe radicals R⁴ or R⁵ is hydrogen and the other radical of R⁴ or R⁵ ismethyl.

A sixth embodiment of the present invention encompasses compounds of theformula (I) in which

-   -   R⁴ and R⁵ preferably together form a (C₂-C₇)-alkylene group        which may comprise one or more oxygen and/or sulfur atoms, where        the (C₂-C₇)-alkylene group may be mono- or polysubstituted by        halogen and the respective halogen substituents may be identical        or different; and    -   R⁴ and R⁵, are particularly preferably —CH₂—CH₂—CH₂— or        —CH₂—CH₂—.

A seventh embodiment of the present invention encompasses compounds ofthe formula (I) in which

-   -   R⁶ and R⁷, independently of one another, are preferably selected        from the group consisting of hydrogen, (C₁-C₆)-alkyl and        (C₆-C₁₄)-aryl;    -   R⁶ and R⁷, independently of one another, are particularly        preferably selected from the group consisting of hydrogen,        methyl and phenyl; and    -   R⁶ and R⁷ are very particularly preferably hydrogen.

An eighth embodiment of the present invention encompasses compounds ofthe formula (I) in which

-   -   R⁸ is preferably selected from the group consisting of hydrogen,        (C₁-C₆)-alkyl or halogen;    -   R⁸ is particularly preferably selected from the group consisting        of hydrogen, methyl or fluorine; and    -   R⁸ is very particularly preferably hydrogen.

A ninth embodiment of the present invention encompasses compounds of theformula (I) in which

-   -   R⁹ is preferably selected from the group consisting of hydrogen        and (C₁-C₆)-alkyl;    -   R⁹ is particularly preferably selected from the group consisting        of hydrogen and methyl; and    -   R⁹ is very particularly preferably hydrogen.

A tenth embodiment of the present invention encompasses compounds of theformula (I) in which

-   -   R¹⁰ is preferably selected from the group consisting of        hydrogen, (C₁-C₆)-alkyl, di(C₁-C₆)-alkylamino, halogen,        (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, (C₁-C₆)-alkyl-(C₂-C₆)-alkynyl,        (C₁-C₆)-alkoxy-(C₁-C₆)-alkyl-(C₂-C₆)-alkynyl, cyano,        (C₁-C₆)-alkoxycarbonyl and aminocarbonyl;    -   R¹⁰ is particularly preferably selected from the group        consisting of hydrogen, methyl, propyl, isopropyl, butyl,        tert-butyl, dimethylamino, fluorine, chlorine, bromine, iodine,        ethenyl, ethynyl, methylethynyl, ethylethynyl, MeOCH₂C═C—,        cyano, COOMe and CONH₂; and    -   R¹⁰ is very particularly preferably hydrogen or methyl.

An eleventh embodiment of the present invention encompasses compounds ofthe formula (I) in which

-   -   R¹¹ is preferably selected from the group consisting of hydrogen        and (C₁-C₆)-alkyl;    -   R¹¹ is particularly preferably selected from the group        consisting of hydrogen and methyl; and    -   R¹¹ is very particularly preferably hydrogen.

A twelfth embodiment of the present invention encompasses compounds ofthe formula (I) in which

-   -   X is preferably selected from the group consisting of CH₂, O,        NH, a chemical bond and S; and    -   X is particularly preferably selected from the group consisting        of CH₂, O and a chemical bond.

Within the context of the present invention, it is possible to combinethe individual preferred, particularly preferred and very particularlypreferred meanings for the substituents R¹ to R¹¹ and X with one anotheras desired. This means that compounds of the formula (I) are encompassedby the present invention in which, for example, the substituent R¹ has apreferred meaning and the substituents R² to R¹¹ have the generalmeaning, or else the substituent R² has a preferred meaning, thesubstituent R³ has a particularly preferred meaning and the othersubstituents have a general meaning.

Within the context of the present invention, the compound of the formula(I) also encompasses compounds which have been quaternized by a)protonation, b) alkylation or c) oxidation on a nitrogen atom.

The compounds of the formula (I) can form salts.

Salt formation can take place as a result of the action of a base onthose compounds of the formula (I) which carry an acidic hydrogen atom,e.g. when R¹ comprises a COOH group or a sulfonamide group —NHSO₂—.Suitable bases are, for example, organic amines, such as trialkylamines,morpholine, piperidine or pyridine, and also ammonium, alkali metal oralkaline earth metal hydroxides, carbonates and hydrogencarbonates, inparticular sodium hydroxide and potassium hydroxide, sodium carbonateand potassium carbonate and sodium hydrogencarbonate and potassiumhydrogencarbonate. These salts are compounds in which the acidichydrogen is replaced by a cation suitable for agriculture, for examplemetal salts, in particular alkali metal salts or alkaline earth metalsalts, in particular sodium salts and potassium salts, and also ammoniumsalts, salts with organic amines or quaternary ammonium salts, forexample with cations of the formula [NRR′R″R′″]⁺, in which R to R′″, ineach case independently of one another, are an organic radical, inparticular alkyl, aryl, aralkyl or alkylaryl. Also suitable arealkylsulfonium and alkylsulfoxonium salts, such as(C₁-C₄)-trialkylsulfonium and (C₁-C₄)-trialkylsulfoxonium salts.

The compounds of the formula (I) can form salts through additionreaction of a suitable inorganic or organic acid, such as, for example,mineral acids, such as, for example, HCl, HBr, H₂SO₄, H₃PO₄ or HNO₃, ororganic acids, for example carboxylic acids, such as formic acid, aceticacid, propionic acid, oxalic acid, lactic acid or salicylic acid, orsulfonic acids, such as, for example, p-toluenesulfonic acid, onto abasic group, such as, for example, amino, alkylamino, dialkylamino,piperidino, morpholino or pyridino. These salts then comprise theconjugated base of the acid as anion.

Suitable substituents which are present in deprotonated form, such as,for example, sulfonic acids or carboxylic acids, can form internal saltswith groups that for their part are protonatable, such as amino groups.

The compounds of the formula (I) and their salts are also referred tobelow for short as “compounds (I)” according to the invention or usedaccording to the invention.

In the formula (I) and all of the other formulae in the presentinvention, the radicals alkyl, alkoxy, haloalkyl, haloalkoxy,alkylamino, alkylthio, haloalkylthio, and the corresponding unsaturatedand/or substituted radicals in the carbon backbone may in each case bestraight-chain or branched. Unless specifically stated, in the case ofthese radicals, preference is given to the lower carbon backbones, e.g.having 1 to 6 carbon atoms, in particular 1 to 4 carbon atoms, or in thecase of unsaturated groups having 2 to 6 carbon atoms, in particular 2to 4 carbon atoms. Alkyl radicals, including in the composite meaningssuch as alkoxy, haloalkyl etc., mean, for example, methyl, ethyl,n-propyl or isopropyl, n-butyl, isobutyl, t-butyl or 2-butyl, pentyls,hexyls, such as n-hexyl, isohexyl and 1,3-dimethylbutyl, heptyls, suchas n-heptyl, 1-methylhexyl and 1,4-dimethylpentyl; alkenyl and alkynylradicals have the meaning of the possible unsaturated radicalscorresponding to the alkyl radicals; where at least one double bond ortriple bond, preferably one double bond or triple bond, is present.Alkenyl is, for example, vinyl, allyl, 1-methylprop-2-en-1-yl,2-methylprop-2-en-1-yl, but-2-en-1-yl, but-3-en-1-yl,1-methylbut-3-en-1-yl and 1-methylbut-2-en-1-yl; alkynyl is, forexample, ethynyl, propargyl, but-2-yn-1-yl, but-3-yn-1-yl and1-methylbut-3-yn-1-yl.

Cycloalkyl groups are, for example, cyclopropyl, cyclobutyl,cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl. The cycloalkylgroups can occur in bi- or tricyclic form.

If haloalkyl groups and haloalkyl radicals of haloalkoxy, haloalkylthio,haloalkenyl, haloalkynyl etc. are given, in these radicals, the lowercarbon backbones, e.g. having 1 to 6 carbon atoms or 2 to 6, inparticular 1 to 4 carbon atoms or preferably 2 to 4 carbon atoms, andalso the corresponding unsaturated and/or substituted radicals in thecarbon backbone are in each case straight-chain or branched. Examplesare difluoromethyl, 2,2,2-trifluoroethyl, trifluoroallyl,1-chloroprop-1-yl-3-yl.

In these radicals, alkylene groups are the lower carbon backbones, e.g.having 1 to 10 carbon atoms, in particular 1 to 6 carbon atoms orpreferably 2 to 4 carbon atoms, and the corresponding unsaturated and/orsubstituted radicals in the carbon backbone, which may in each case bestraight-chain or branched. Examples are methylene, ethylene,n-propylene and isopropylene and n-butylene, sec-butylene, isobutylene,t-butylene.

In these radicals, hydroxyalkyl groups are the lower carbon backbones,e.g. having 1 to 6 carbon atoms, in particular 1 to 4 carbon atoms, andthe corresponding unsaturated and/or substituted radicals in the carbonbackbone, which may in each case be straight-chain or branched. Examplesthereof are 1,2-dihydroxyethyl and 3-hydroxypropyl.

Halogen is fluorine, chlorine, bromine or iodine. Haloalkyl, haloalkenyland halo-alkynyl are alkyl, alkenyl or alkynyl, respectively, partiallyor completely substituted by halogen, preferably by fluorine, chlorineor bromine, in particular by fluorine and/or chlorine, e.g.monohaloalkyl, perhaloalkyl, CF₃, CHF₂, CH₂F, CF₃CF₂, CH₂FCHCl, CCl₃,CHCl₂, CH₂CH₂Cl; haloalkoxy is e.g. OCF₃, OCHF₂, OCH₂F, CF₃CF₂O, OCH₂CF₃and OCH₂CH₂Cl; the same applies for haloalkenyl and other radicalssubstituted by halogen.

Aryl is a mono-, bi- or polycyclic aromatic system, for example phenylor naphthyl, preferably phenyl.

Primarily for reasons of higher herbicidal effect, better selectivityand/or better producibility, compounds of the formula (I) according tothe invention or their agrochemical salts or quaternary N derivativesare of particular interest in which individual radicals have one of thepreferred meanings already specified or specified below, or inparticular those in which one or more of the preferred meanings alreadyspecified or specified below occur in combination.

The radical definitions given above in general or given in preferredranges apply both for the end products of the formula (I) and alsocorrespondingly for the starting materials and intermediates required ineach case for the preparation. These radical definitions can beexchanged among one another, and also between the stated preferredranges.

The present compounds of the formula (I) have a chiral carbon atom whichis shown in the structure depicted below by the symbol (*):

According to the rules in accordance with Cahn, Ingold and Prelog (CIPrules), this carbon atom can have either an (R) configuration or an (S)configuration.

The present invention encompasses compounds of the formula (I) both with(S) and with (R) configuration, i.e. the present invention encompassesthe compounds of the formula (I) in which the carbon atom in questionhas

-   -   (1) an (R) configuration; or    -   (2) an (S) configuration.

Moreover, the present invention also encompasses

-   -   (3) any desired mixtures of compounds of the formula (I) which        have an (R) configuration (compounds of the formula (I-(R)),        with compounds of the formula (I) which have an (S)        configuration (compounds of the formula (I-(S)),        where a racemic mixture of the compounds of the formula (I)        with (R) and (S) configuration is likewise encompassed by the        present invention.

However, within the context of the present invention, preference isgiven in particular to compounds of the formula (I) having (R)configuration with a selectivity of 60 to 100%, preferably 80 to 100%,in particular 90 to 100%, very particularly 95 to 100%, where theparticular (R) compound is present with an enantioselectivity of in eachcase more than 50% ee, preferably 60 to 100% ee, in particular 80 to100% ee, very particularly 90 to 100% ee, most preferably 95 to 100% ee,based on the total content of (R) compound in question.

Consequently, the present invention relates in particular to compoundsof the formula (I) in which the stereochemical configuration on thecarbon atom indicated by (*) is present with a stereochemical purity of60 to 100% (R), preferably 80 to 100% (R), in particular 90 to 100% (R),very particularly 95 to 100% (R).

Taking into consideration the Cahn, Ingold and Prelog rules, on thecarbon atom indicated by (*), a situation may also arise in which, onaccount of the priority of the respective substituents, the (S)configuration is preferred on the carbon atom indicated by (*). This isthe case, for example, when the radicals R⁴ and/or R⁵ are a C₁-C₆-alkoxyradical.

Consequently, within the context of the present invention, preference isgiven in particular to compounds of the formula (I) which, in theirspatial arrangement, correspond to those compounds of the formula (I)where R⁴ and R⁵=hydrogen with (R) configuration, with a selectivity of60 to 100%, preferably 80 to 100%, in particular 90 to 100%, veryparticularly 95 to 100%, where the particular (R)-analogous compound ispresent with an enantioselectivity of in each case more than 50% ee,preferably 60 to 100% ee, in particular 80 to 100% ee, very particularly90 to 100% ee, most preferably 95 to 100% ee, based on the total contentof (R)-analogous compound in question. Consequently, the presentinvention relates in particular to compounds of the formula (I) in whichthe stereochemical configuration on the carbon atom indicated by (*) ispresent with a stereochemical purity of 60 to 100% (R, or analogous-R),preferably 80 to 100% (R, or analogous-R), in particular 90 to 100% (R,or analogous-R), very particularly 95 to 100% (R, or analogous-R).

In particular, the compounds of the formula (I) according to theinvention can also have further chirality centers on the carbon atomsindicated by (**) and (***):

Within the context of the present invention, any desired stereochemicalconfigurations on the carbon atoms indicated by (*), (**) and (***) arepossible:

Configuration of Configuration of Configuration of carbon atom (*)carbon atom (**) carbon atom (***) R R R R R S R S R S R R R S S S R S SS R S S S

Moreover, depending on the selection of the particular radicals, furtherstereoelements may be present in the compounds of the formula (I)according to the invention.

If, for example, one or more alkenyl groups are present, thendiastereomers (Z and E isomers) can occur.

If, for example, one or more asymmetric carbon atoms are present, thenenantiomers and diastereomers can occur.

Corresponding stereoisomers can be obtained from the mixtures producedduring the preparation by customary separation methods, for example bychromatographic separation methods. Stereoisomers can likewise beselectively prepared by employing stereoselective reactions usingoptically active starting materials and/or auxiliaries. The inventionthus also relates to all stereoisomers which are encompassed by theformula (I), but are not stated with their specific stereoform, andmixtures thereof.

The combination possibilities of the various substituents of the formula(I) are to be understood such that the general principles ofconstructing chemical compounds are observed, i.e. the formula (I) doesnot encompass compounds which the person skilled in the art knows arenot chemically possible.

The table below gives specific examples of the compounds of the formula(I) according to the invention:

TABLE Stereo Stereo R¹ R² R³ N, R³ R⁴ R⁵ R⁴, R⁵ R⁶ R⁷ 1.1. H Ph H R CH₃H H H 1.2. H 2-CH₃-Ph H R CH₃ H H H 1.3. H CH₃ H rac H H H H 1.4. H CH₃H rac H H H H 1.5. H CH₃ H rac H H H H 1.6. H CH₃ H rac H H H H 1.7. HCH₃ H rac H H H H 1.8. H CH₃ H rac H H H H 1.9. H CH₃ H rac H H H H1.10. H CH₃ H rac H H H H 1.11. H CH₃ H rac H H H H 1.12. H CH₃ H rac HH H H 1.13. H CH₃ H rac H H H H 1.14. H CH₃ H rac CH₃ H rac H H 1.15. HCH₃ H rac H H H H 1.16. H CH₃ H rac CH₃ H rac H H 1.17. H CF₃ H rac H HH H 1.18. H CF₃ H rac H H H H 1.19. OCH₃ CF₃ H rac H H H H 1.20. OCH₃CF₂H H rac H H H H 1.21. OCH₃ CF₃ H rac CH₃ H rac H H 1.22. OCH₂CH₃ CF₃H rac CH₃ H rac H H 1.23. OCH₃ CF₂H H rac CH₃ H rac H H 1.24. OCH₃ CF₃ Hrac H H H H 1.25. CH₃ CF₃ H rac H H H H 1.26. CH₃ CF₃ H rac H H H H1.27. H CF₃ H R CH₃ H S H H 1.28. H CClF₂ H R CH₃ H S H H 1.29. H CF₃ HR CH₃ H S H H 1.30. H CF₂H H R CH₃ H S H H 1.31. H CF₃ H rac CH₃ H rac HH 1.32. H CH₃ H R CH₃ H S H H 1.33. H CH₃ H R H H H H 1.34. H CF₃ H R HH H H 1.35. H CF₂H H R H H H H 1.36. H CF₂H H R H H H H 1.37. I H H R HH H H 1.38. Cl CF₃ H R CH₃ H S H H 1.39. CH₃ CH₃ H R CH₃ H S H H 1.40. ICF₃ H R CH₃ H S H H 1.41. OCH₃ CF₃ H R CH₃ H S H H 1.42. H Cl H R CH₃ HS H H 1.43. H Cl H R H H H H 1.44. H Cl H R H H H H 1.45. OCH₃ CF₃ H R HH H H 1.1. H CF₃ H R CH₂CH₃ H S H H 1.46. Cl CF₃ H R H H H H 1.47. HOCH₃ H R CH₃ H S H H 1.48. H OCH₃ H R H H H H 1.49. H OCH₃ H R H H H H1.50. CN -Ph H R CH₃ H S H H 1.51. CF₃ CF₂—CF₃ H R H H H H 1.52. CN Ph HR H H H H 1.53. CN CH₃ H R CH₃ H S H H 1.54. CN OCH₂CH₃ H R H H H H1.55. CN OCH₂CH₃ H R CH₃ H S H H 1.56. CF₃ H H R CH₃ H S H H 1.57. CF₃ HH R H H H H 1.58. Cl CH₃ H R H H H H 1.59. Cl CH₃ H R CH₃ H S H H 1.60.Br CH₃ H R CH₃ H S H H 1.61. Br CH₃ H R H H H H 1.62. H C(═O)OCH₃ H RCH₃ H S H H 1.63. CF₃ CF₂—CF₃ H R H H H H 1.64. NO₂ CH₃ H R CH₃ H S H H1.65. NO₂ CH₃ H rac H H H H 1.66. Br CH₃ H R H H H H 1.67. Br CH₃ H racH H H H 1.68. Br CH₃ H rac H H H H 1.69. CN CH₃ H rac H H H H 1.70. C≡CHCH₃ H rac H H H H 1.71. C≡CCH₃ CH₃ H rac H H H H 1.72. CN CH₃ H R H H HH 1.73. C≡CH CH₃ H R H H H H 1.74. C≡CCH₃ CH₃ H R H H H H 1.75. C≡CH CH₃H R H H H H 1.76. C(═O)CH₃ CH₃ H R H H H H 1.77. Br CH₂CH₃ H R CH₃ H S HH 1.78. Br CF₃ H R CH₃ H S H H 1.79. Br CF₂H H R CH₃ H S H H 1.80. CNCF₃ H R CH₃ H S H H 1.81. CN CF₂H H R CH₃ H S H H 1.82. CCH CF₃ H R CH₃H S H H 1.83. C(═O)CH₃ CF₃ H R CH₃ H S H H 1.84. C(═O)CH₃ CF₂H H R CH₃ HS H H 1.85. CN CFH₂ H R CH₃ H S H H 1.86. Br CFH₂ H R CH₃ H S H H 1.87.Br CF₂H H R H H H H 1.88. Br CF₂H H R H H H H 1.89. CN CF₂H H R H H H H1.90. C≡CH CF₂H H R H H H H 1.91. C≡CCH₃ CF₂H H R H H H H 1.92. C≡CHCF₂H H R H H H H 1.93. Br CF₂H H R H H H H 1.94. H CN H R CH₃ H S H H1.95. H C(═O)NH₂ H R CH₃ H S H H 1.96. H C(═O)N(CH₃)₂ H R CH₃ H S H H1.97. C(═O)NH₂ Cl H R CH₃ H S H H 1.98. C(═O)NH₂ Br H R CH₃ H S H H1.99. CN N(CH₃)₂ H R CH₃ H S H H 1.100. CH₃ N(CH₃)₂ H R CH₃ H S H H1.101. Cl N(CH₃)₂ H R CH₃ H S H H 1.102. Cl N(CH₂CH₃)₂ H R CH₃ H S H H1.103. Cl N-Morpholine H R CH₃ H S H H 1.104. Cl N(CH₃)₂ H R H H H H1.105. Cl N(CH₃)₂ H R H H H H 1.106. Cl N(CH₃)₂ H R H H H H 1.107. ClN(CH₃)₂ H rac H H H H 1.108. Cl N(CH₃)₂ H rac H H H H 1.109. Cl N(CH₃)₂CH₃ rac H H H H 1.110. Cl H CH₃ rac H H H H 1.111. Cl H H rac H H H H1.112. Br H H rac H H H H 1.113. CF₃ H H rac H H H H 1.114. CN H H rac HH H H 1.115. CN H H rac H H H H 1.116. CN H H rac H H H H 1.117. CNN(CH₃)₂ H rac H H H H 1.118. CH₃ N(CH₃)₂ H rac H H H H 1.119. CH₃ OCH₃ Hrac H H H H 1.120. CH₃ OCH₂CCH H rac H H H H 1.121. Cl OCH₂CCH H rac H HH H 1.122. Br OCH₂CH₃ H rac H H H H 1.123. H CH₃ H rac CH₃ H rac H H1.124. H CH₃ H rac H H H H 1.125. H CH₃ H rac H H H H 1.126. H CH₃ H racH H H H 1.127. H OCH₃ H rac H H H H 1.128. H OCH₃ H rac H H H H 1.129.Cl CF₃ H rac H H CH₃ H 1.130. Cl CF₂H H rac H H CH₃ H 1.131. Cl CH₃ Hrac —CH₂—CH₂— H H 1.132. Br CH₃ H rac —CH₂—CH₂— H H 1.133. CN CH₃ H rac—CH₂—CH₂— H H 1.134. C≡CH CH₃ H rac —CH₂—CH₂— H H 1.135. Cl CH₃ H racCH₃ CH₃ H H 1.136. Br CH₃ H rac CH₃ CH₃ H H 1.137. CN CH₃ H rac CH₃ CH₃H H 1.138. C≡CCH₃ CH₃ H rac CH3 CH₃ H H 1.139. C≡CH CH₃ H rac CH₃ CH₃ HH 1.140. C(═O)CH₃ CH₃ H rac CH₃ CH₃ H H 1.141. OCH₃ CH₂OCH₃ H rac CH₃ Hrac H H 1.142. OCH₃ H H rac CH₃ H rac H H 1.143. OCH₃ H H rac CH₃ H racH H 1.144. OCH₃ H H rac H H CH₃ H 1.145. OCH₃ H H rac H H CH₃ H 1.146.OCH₃ CH₂OCH₃ H rac H H CH₃ H 1.147. CH₃ CH₃ H rac CH₃ H rac H H 1.148.CH₃ OCH₃ H rac CH₃ H rac H H 1.149. CH₃ H H rac CH₃ H rac H H 1.150. CH₃H H rac CH₂CH₃ H rac H H 1.151. CH₃ H H rac CH₃ H rac H H 1.152. CH₃ H Hrac CH₃ H rac H H 1.153. CH₃ H H rac OCH₃ H rac H H 1.154. CH₃ H H rac HH H H 1.155. CH₃ H H rac H H H H 1.156. CH₃ H H rac H H H H 1.157. CH₃ HH rac H H H H 1.158. CH₃ H H rac H H H H 1.159. CH₃ H H rac H H H H1.160. H 2F-Ph H R CH₃ H S H H 1.161. H 2F,4CH₃-PH H R CH₃ H S H H1.162. CN 2,4-F-Ph H H CH₃ H S H H 1.163. CN 4CH₃-Ph H R CH₃ H S H H1.164. CN 4F-Ph H R H H H H 1.165. Br 4CH₃-Ph H H CH₃ H S H H 1.166.C≡CH 4CH₃-Ph H H CH₃ H S H H 1.167. Br 2CH₃-Ph H R CH₃ H S H H 1.168. CN2CH₃-Ph H R CH₃ H S H H 1.169. C≡CH 2CH₃-Ph H R CH₃ H S H H 1.170.C(═O)CH₃ 2CH₃-Ph H R CH₃ H S H H 1.171. H 2CH₃-Ph H R H H H H 1.172. Br2CH₃-Ph H R H H H H 1.173. CN 2CH₃-Ph H R H H H H 1.174. C≡CH 2CH₃-Ph HR H H H H 1.175. H 2CH₃-Ph H rac H H H H 1.176. H 2CH₃-Ph H rac H H H H1.177. H 2CH3-Ph H rac H H H H 1.178. H 2CH₃-Ph H rac H H H H 1.179. H2CH₃-Ph H rac H H H H 1.180. H 2CH₃-Ph H rac H H H H 1.181. O≡CH 2CH₃-PhH rac H H H H 1.182. H 2CH₃-Ph H rac H H H H 1.183. Br 2Cl-Ph H rac H HH H 1.184. CN 2Cl-Ph H rac H H H H 1.185. H 2F-Ph H rac H H H H 1.186.Br 2F-Ph H rac H H H H 1.187. Br 2Cl-Ph H rac H H H H 1.188. Br 2OCH₃-PhH rac H H H H 1.189. H 2OCH₃-Ph H rac H H H H 1.190. Br 2,4-OCH₃-Ph Hrac H H H H 1.191. H 2N(CH₃)₂-Ph H rac H H H H 1.192. H 4N(CH₃)₂-Ph Hrac H H H H 1.193. H 2N(CH₃)₂-Ph H R H H H H 1.194. H 2CH₃-Ph H rac H HCH₃ H 1.195. H Ph H rac H H CH₃ H 1.196. H Ph H rac H H CH₃ H 1.197. HPh H rac H H CH₃ H 1.198. H 4F-Ph H rac H H CH₃ H 1.199. H 2,4CH₃-Ph Hrac H H CH₃ H 1.200. H CH₂CH₃ H R CH₃ H S H H 1.201. H CH(CH₃)₂ H R CH₃H S H H 1.202. H CH2CH₃ H R H H H H 1.203. H CH(CH₃)₂ H R H H H H 1.204.H C(CH₃)₃ H R H H H H 1.205. CN NH₂ H R H H H H 1.206. CN OCH₃ H R H H HH 1.207. H O-(4-FPh) H R CH₃ H S H H 1.208. H O-(3-Cl, 4-FPh) H R CH₃ HS H H 1.209. Cl CF₃ H rac H H H H 1.210. CF₃ H H R H H H H 1.211. CF₃ HH rac H H H H 1.212. CF₃ H H rac H H H H 1.213. CF₃ H H rac H H H H1.214. CF₃ H H rac H H CH₃ CH₃ 1.215. CF₃ H H rac CH₃ H rac H H 1.216.CF₃ H H rac CH₃ H rac H H 1.217. CF₃ H H rac H H H H 1.218. CF₃ H H racH H H H 1.219. CF₃ H H rac H H H H 1.220. H CF₃ H R H H H H 1.221. H CF₃H rac H H H H 1.222. C(═O)O- CH₃ H R H H H H cyclohexyl 1.223. CF₃ OCH₃H R CH₃ H S H H 1.224. CF₃ OCH₃ H R H H H H 1.225. CF₃ H H S OH H R H H1.226. CF₃ H H S OH H S H H 1.227. CF₃ H H S OCH₃ H R H H 1.228. CF₃ H HS OCH₃ H S H H 1.229. CF₃ H H rac H H H H 1.230. CF₃ H H rac H H H H1.231. CF₃ H H rac H H H H 1.232. CF₃ H H rac H H H H 1.233. CF₂H H H RH H H H 1.234. SCH₃ CH₃ H R CH₃ H S H H 1.235. S(═O)CH3 CH3 H R CH3 H SH H 1.236. S(═O)2CH3 CH3 H R CH3 H S H H 1.237. C(═O)CH3 CH3 H R CH3 H SH H 1.238. C(═O)CH3 H H R CH3 H S H H 1.239. C≡CH H H R CH3 H S H H1.240. C≡CC(CH3)3 H H R CH3 H S H H 1.241. C≡CSiCH3)3 H H R CH3 H S H H1.242. C≡CH CH3 H R CH3 H S H H 1.243. C≡CSi(CH3)3 CH3 H R CH3 H S H H1.244. CCSi(CH3)3 CH3 H R H H H H 1.245. C(═O)CH3 H H R H H H H 1.246.C≡CH H H R H H H H 1.247. C≡C—C(CH3)3 H H R H H H H 1.248. C≡C—Si(CH3)3H H R H H H H 1.249. C≡C-Ph H H R H H H H 1.250. Cl C(═O)OCH3 H R CH3 HH H 1.251. Cl C(═O)OCH3 H R H H H H 1.252. Cl CN H R CH3 H H H 1.253. ClC(═O)NH2 H R H H H H 1.254. Cl CN H R H H H H 1.255. CF3 OCH3 H R H H HH 1.256. CF3 OCH3 H rac H H H H 1.257. CF3 OCH2CH3 H R H H H H 1.258.CF3 OCH3 H rac H H H H 1.259. CF3 OCH(CH3)2 H rac H H H H Stereo R⁶, R⁷R⁸ R⁹ R¹⁰ R¹¹ X 1.1. H H CH₃ H — 1.2. H H CH₃ H — 1.3. CH₃ H CH₃ H —CH₂—1.4. H H H H — 1.5. H H F H — 1.6. H H CH₂CH₃ H — 1.7. H H Br H — 1.8. HH CN H — 1.9. H H CCH H — 1.10. H H C(═O)NH₂ H — 1.11. H H C(═O)N(CH₃)₂H — 1.12. H H CH═CH₂ H — 1.13. H H CCCH₃ H — 1.14. H H CCH H — 1.15. H HI H — 1.16. H H I H — 1.17. CH₃ H CH₃ H —CH₂— 1.18. H H H H — 1.19. H HH H — 1.20. H H H H — 1.21. H H CH₃ H — 1.22. H H CH₃ H — 1.23. H H Cl H— 1.24. CH₃ H CH₃ H —CH₂— 1.25. CH₃ H CH₃ H —CH₂— 1.26. H H H H — 1.27.H H CH₃ H — 1.28. H H CH₃ H — 1.29. H H CH₂CH₃ H — 1.30. H H CH₃ H —1.31. H H CH₃ H — 1.32. H H CH₃ H — 1.33. H H H H —CH₂— 1.34. H H H H—CH₂— 1.35. H H H H —CH₂— 1.36. H H H H — 1.37. H H H H —CH₂— 1.38. H HCH₃ H — 1.39. H H CH₃ H — 1.40. H H CH₃ H — 1.41. H H CH₃ H — 1.42. H HCH₃ H — 1.43. H H H H —CH₂— 1.44. H H H H — 1.45. H H H H —CH₂— 1.1. H HCH₃ H — 1.46. H H H H —CH₂— 1.47. H H CH₃ H — 1.48. H H H H —CH₂— 1.49.H H H H — 1.50. H H CH₃ H — 1.51. H H H H — 1.52. H H H H —CH₂— 1.53. HH CH₃ H — 1.54. H H H H —CH₂— 1.55. H H CH₃ H — 1.56. H H CH₃ H — 1.57.H H H H —CH₂— 1.58. H H H H —CH₂— 1.59. H H CH₃ H — 1.60. H H CH₃ H —1.61. H H H H —CH₂— 1.62. H H CH₃ H — 1.63. H H H H — 1.64. H H CH₃ H —1.65. H H H H — 1.66. H H H H —O— 1.67. CH₃ H H H —O— 1.68. CH₃ H CH₃ H—O— 1.69. CH₃ H H H —O— 1.70. CH₃ H H H —O— 1.71. CH₃ H H H —O— 1.72. HH H H —O— 1.73. H H H H —O— 1.74. H H H H —O— 1.75. H H H H —CH₂— 1.76.H H H H —CH₂— 1.77. H H CH₃ H — 1.78. H H CH₃ H — 1.79. H H CH₃ H —1.80. H H CH₃ H — 1.81. H H CH₃ H — 1.82. H H CH₃ H — 1.83. H H CH₃ H —1.84. H H CH₃ H — 1.85. H H CH₃ H — 1.86. H H CH₃ H — 1.87. H H H H —1.88. H H CH₂CH₃ H — 1.89. H H H H — 1.90. H H H H — 1.91. H H H H —1.92. H H CH₃ H — 1.93. H H CH₃ H — 1.94. H H CH₃ H — 1.95. H H CH₃ H —1.96. H H CH₃ H — 1.97. H H CH₃ H — 1.98. H H CH₃ H — 1.99. H H CH₃ H —1.100. H H CH₃ H — 1.101. H H CH₃ H — 1.102. H H CH₃ H — 1.103. H H CH₃H — 1.104. H H H H — 1.105. H H H H —CH₂— 1.106. H H H H —O— 1.107. CH₃H CH₃ H —O— 1.108. CH₃ H H CH₃ —O— 1.109. H H H H —CH₂— 1.110. H H H H—CH₂— 1.111. H H H H —CH₂— 1.112. H H H H —CH₂— 1.113. H H CH₃ H —CH₂—1.114. H H CH₃ H —CH₂— 1.115. H H CH₃ H —O— 1.116. F H CH₃ H —O— 1.117.F H H H —O— 1.118. H H H H —CH₂— 1.119. H H H H —CH₂— 1.120. H H H H—CH₂— 1.121. H H H H —CH₂— 1.122. H H H H —CH₂— 1.123. H H Cl H — 1.124.H H Cl H — 1.125. H F F H — 1.126. H OCH₃ OCH₃ H — 1.127. H OCH₃ OCH₃ H— 1.128. CH₃ H H H — 1.129. rac H H H H — 1.130. rac H H H H — 1.131. HH H H — 1.132. H H H H — 1.133. H H H H — 1.134. H H H H — 1.135. H H HH — 1.136. H H H H — 1.137. H H H H — 1.138. H H H H — 1.139. H H H H —1.140. H H H H — 1.141. H H H H — 1.142. H H H H — 1.143. H H H H —CH₂—1.144. rac H H CH3 H —O— 1.145. rac H H F H —O— 1.146. rac H H F H —O—1.147. H H H H — 1.148. H H H H — 1.149. H H H H — 1.150. H H H H —1.151. H H CH₂CH₃ H — 1.152. H H CH(CH₃)₂ H — 1.153. H H H H — 1.154. HH I H — 1.155. H H CN H — 1.156. H H CCH H — 1.157. H H C(═O)NH₂ H —1.158. H H C(═O)OH H — 1.159. H H C(═O)CH₃ H — 1.160. H H CH₃ H — 1.161.H H CH₃ H — 1.162. H H CH₃ H — 1.163. H H CH₃ H — 1.164. H H H H —CH₂—1.165. H H CH₃ H —CH₂— 1.166. H H CH₃ H — 1.167. H H CH₃ H — 1.168. H HCH₃ H — 1.169. H H CH₃ H — 1.170. H H CH₃ H — 1.171. H H H H —CH₂—1.172. H H H H —CH₂— 1.173. H H H H —CH₂— 1.174. H H H H —CH₂— 1.175.CH₃ H H H —O— 1.176. CH₃ H CH₃ H —O— 1.177. CH₃ H H H —O— 1.178. CH₃ H HH —O— 1.179. CH₃ H H H —O— 1.180. CH₃ H H H —O— 1.181. CH₃ H H H —O—1.182. CH₃ H H H —O— 1.183. CH₃ H H H —O— 1.184. CH₃ H H H —O— 1.185.CH₃ H H H —O— 1.186. CH₃ H CH₃ H —O— 1.187. CH₃ H H CH₃ —O— 1.188. CH₃ HH H —O— 1.189. CH₃ H H H —O— 1.190. CH₃ H H H —O— 1.191. CH₃ H H H —O—1.192. CH₃ H H H —O— 1.193. H H H H —O— 1.194. rac H H H H —O— 1.195.rac H H CH₃ H —O— 1.196. rac CH₃ H CH₃ H —O— 1.197. rac F H H H —O—1.198. rac H H CH₃ H —O— 1.199. rac H H CH₃ H —O— 1.200. H H CH₃ H —1.201. H H CH₃ H — 1.202. H H H H —CH₂— 1.203. H H H H —CH₂— 1.204. H HH H —CH₂— 1.205. H H H H —CH₂— 1.206. H H H H —CH₂— 1.207. H H CH₃ H —1.208. H H CH₃ H — 1.209. H H H H — 1.210. H H H H — 1.211. H H CH₂CH₃ H—O— 1.212. H H OCH₃ H —O— 1.213. H H OCH₃ H —CH₂— 1.214. H Cl F H —O—1.215. H H F H — 1.216. H Cl H H — 1.217. H Cl H H — 1.218. H H H H—CH₂— 1.219. CH₃ H H H — 1.220. H H H H — 1.221. CH₃ H H H — 1.222. H HH H —CH₂— 1.223. H H CH₃ H — 1.224. H H H H —₂2— 1.225. H H H H — 1.226.H H H H — 1.227. H H H H — 1.228. H H H H — 1.229. F H H H —O— 1.230.CH₃ H H H —O— 1.231. H OCH₃ OCH₃ H — 1.232. H OCH₂O H — 1.233. H H CH₃ H— 1.234. H H CH₃ H — 1.235. H H CH3 H — 1.236. H H CH3 H — 1.237. H HCH3 H — 1.238. H H CH3 H — 1.239. H H CH3 H — 1.240. H H CH3 H — 1.241.H H CH3 H — 1.242. H H CH3 H — 1.243. H H CH3 H — 1.244. H H H H —CH2—1.245. H H H H —CH2— 1.246. H H H H —CH2— 1.247. H H H H —CH2— 1.248. HH H H —CH2— 1.249. H H H H —CH2— 1.250. H H CH3 H — 1.251. H H H H —CH2—1.252. H H CH3 H — 1.253. H H H H —CH2— 1.254. H H H H —CH2— 1.255. H HH H — 1.256. H H CH2CH3 H —O— 1.257. H H H H —CH2— 1.258. H H CH(CH3)2 H— 1.259. H H CH(CH3)2 H —

The present invention further provides processes for the preparation ofcorresponding compounds of the formula (I) and/or their salts and/ortheir agrochemically compatible quaternized nitrogen derivatives:

-   a.) for the preparation of compounds of the formula (I)

-   -   in which the radicals R¹ to R¹¹ and X have the above meanings,        it is possible to react a compound of the formula (II)

-   -   in which R¹ and R² have the above meaning and Z¹ is an        exchangeable radical or a leaving group, such as in particular        chlorine, trichloromethyl, (C₁-C₄)-alkylsulfonyl, unsubstituted        or substituted phenyl-(C₁-C₄)-alkylsulfonyl or        (C₁-C₄)-alkylphenylsulfonyl, with an amine of the formula (III)        or an acid addition salt thereof.

where the radicals R³ to R¹¹ and X have the above meaning.

The compounds of the formula (II) can be obtained for Z=chlorine byreacting compounds of the formula (IV) with ammonia in accordance withthe following reaction scheme:

The resulting isomer mixture of (II) and (V) can be separated bychromatography or be used as a mixture in the subsequent reaction.

The amines of the formula (III) or the acid addition salt thereof arecommercially available and their synthesis is described in WO2004/069814 A1.

The pyrimidines of the formula (II) are commercially available specialderivatives can be prepared by known processes. For example,

-   -   a. the corresponding 4-hydroxypyrimidines can be prepared in        accordance with the publication by Perez et al., Synthesis        1983, p. 402 from cyanacetamide and N-cyanocarboximidoates, and        these can then be subsequently converted, for example with        phosphorus oxychloride, to the compounds of the formula (II);    -   b. 4-hydroxypyrimidines can be prepared from acetoacetic esters        in accordance with the process published by Gershon et al., J.        Heterocyclic Chem., 20, 219 (1983) and J. Heterocycl. Chem.,        21(4), (1984), 1161, and be converted into chloropyrimidines.

-   b.) For the preparation of compounds of the formula (I), compounds    can be used as precursors and be converted as described below into    other compounds according to the invention:    -   (1) For example, derivatives of the formula (I) where R¹, R² or        R¹⁰=halogen, in particular iodine or bromine, can be reacted        with acetylenes or trimethylsilyl-protected acetylene with        transition metal catalysis, e.g. with        bis(triphenylphosphine)palladium(II) chloride, in protic or        aprotic solvents and the addition of a base at temperatures        between 20 and 150° C. to give compounds of the formula (I)        where R¹, R² or R¹⁰=alkynyl.    -   (2) For example, derivatives of the formula (I) where R¹═CN can        be saponified with acidic or basic catalysis; the carboxylic        acids obtained in this way can be converted by known processes        into acid chlorides and, in turn, these can be converted into        amides.    -   (3) For example, derivatives of the formula (I) where R²=Hal can        be converted in protic or aprotic solvents and the addition of a        base at temperatures between 100 and 250° C. through reaction        with alcoholates or amines to give compounds of the formula (I)        where R²=alkoxyalkyl or aminoalkyl or diaminoalkyl.

Collections of compounds of the formula (I) and/or salts thereof whichcan be synthesized by the aforementioned reactions can also be preparedin a parallel manner, it being possible for this to take place in amanual, partly automated or completely automated manner. In thisconnection, it is, for example, possible to automate the reactionprocedure, the work-up or the purification of the products and/orintermediates. Overall, this is understood as meaning a procedure asdescribed, for example, by D. Tiebes in CombinatorialChemistry—Synthesis, Analysis, Screening (editor Günther Jung), VerlagWiley 1999, on pages 1 to 34.

For the parallel reaction procedure and work-up, it is possible to use aseries of commercially available instruments, for example Calpysoreaction blocks from Barnstead International, Dubuque, Iowa 52004-0797,USA or reaction stations from Radleys, Shirehill, Saffron Walden, Essex,CB 11 3AZ, England or MultiPROBE Automated Workstations from PerkinElmer, Waltham, Mass. 02451, USA. For the parallel purification ofcompounds of the formula (I) and salts thereof or of intermediatesproduced during the preparation, there are available, inter alia,chromatography apparatuses, for example from ISCO, Inc., 4700 SuperiorStreet, Lincoln, Nebr. 68504, USA.

The apparatuses listed lead to a modular procedure in which theindividual process steps are automated, but between the process stepsmanual operations have to be carried out. This can be circumvented byusing partly or completely integrated automation systems in which therespective automation modules are operated, for example, by robots.Automation systems of this type can be acquired, for example, fromCaliper, Hopkinton, Mass. 01748, USA.

The implementation of single or several synthesis steps can be supportedthrough the use of polymer-supported reagents/scavenger resins. Thespecialist literature describes a series of experimental protocols, forexample in ChemFiles, Vol. 4, No. 1, Polymer-Supported Scavengers andReagents for Solution-Phase Synthesis (Sigma-Aldrich).

Besides the methods described here, the preparation of compounds of theformula (I) and salts thereof can take place completely or partially bysolid-phase supported methods. For this purpose, individualintermediates or all intermediates in the synthesis or a synthesisadapted for the corresponding procedure are bonded to a synthesis resin.Solid-phase supported synthesis methods are sufficiently described inthe specialist literature, e.g. Barry A. Bunin in “The CombinatorialIndex”, Verlag Academic Press, 1998 and CombinatorialChemistry—Synthesis, Analysis, Screening (editor Günther Jung), VerlagWiley, 1999. The use of solid-phase supported synthesis methods permitsa series of protocols known in the literature, which again can becarried out manually or in an automated manner. The reactions can becarried out, for example, by means of IRORI technology in microreactorsfrom Nexus Biosystems, 12140 Community Road, Poway, CA92064, USA.

Both on a solid phase and in liquid phase can the procedure ofindividual or several synthesis steps be supported through the use ofmicrowave technology. The specialist literature describes a series ofexperimental protocols, for example in Microwaves in Organic andMedicinal Chemistry (editor C. O. Kappe and A. Stadler), Verlag Wiley,2005.

The preparation according to the process described here producescompounds of the formula (I) and their salts in the form of substancecollections which are called libraries. The present invention alsoprovides libraries which comprise at least two compounds of the formula(I) and their salts.

On account of the herbicidal property of the compounds of the formula(I), the invention also further provides the use of the compounds of theformula (I) according to the invention as herbicides for controllingharmful plants.

Herbicides are used in agriculturally utilized crops during variouscultivation phases. For example, the application of some products eventakes place before or during sowing. Others are applied before the cropplant emerges, i.e. before the seedling breaks through the earth'ssurface (pre-emergence herbicides). Finally, post-emergence herbicidesare used if either already the seed leaves or foliage leaves have beenformed by the crop plant.

Here, the compounds according to the invention can be used eitherpre-emergence or post-emergence, with use of the compounds according tothe invention pre-emergence being preferred.

The pre-emergence treatment includes both the treatment of the areaunder cultivation prior to sowing (ppi=pre plant incorporation), andalso the treatment of the sown areas of cultivation which do not yetsustain any growth.

The compounds of the formula (I) according to the invention and theirsalts, also referred to synonymously below together as compounds of theformula (I), have excellent herbicidal effectiveness in respect of abroad spectrum of economically important monocotyledonous anddicotyledonous harmful plants. Difficult-to-control perennial weedswhich produce shoots from rhizomes, root stocks or other perennialorgans are also well controlled by the active ingredients. Here, it isunimportant whether the substances are applied in the presowing method,pre-emergence method or post-emergence method.

Specifically, examples which may be mentioned are some of therepresentatives of the monocotyledonous and dicotyledonous weed florawhich can be controlled by the compounds of the formula (I) according tothe invention, without a limitation to certain species being intendedthrough the naming.

On the side of the monocotyledonous weed species, e.g. Agrostis,Alopecurus, Apera, Avena, Brachicaria, Bromus, Dactyloctenium,Digitaria, Echinochloa, Eleocharis, Eleusine, Festuca, Fimbristylis,Ischaemum, Lolium, Monochoria, Panicum, Paspalum, Phalaris, Phleum, Poa,Sagittaria, Scirpus, Setaria, Sphenoclea, and also Cyperus speciespredominantly from the annual group and on the sides of the perennialspecies Agropyron, Cynodon, Imperata and Sorghum and also perennialCyperus species are well controlled.

In the case of dicotyledonous weed species, the spectrum of actionextends to species such as, for example, Galium, Viola, Veronica,Lamium, Stellaria, Amaranthus, Sinapis, Ipomoea, Matricaria, Abutilonand Sida on the annual side, and Convolvulus, Cirsium, Rumex andArtemisia in the case of the perennial weeds. Moreover, herbicidaleffect in the case of dicotyledonous weeds such as Ambrosia, Anthemis,Carduus, Centaurea, Chenopodium, Cirsium, Convolvulus, Datura, Emex,Galeopsis, Galinsoga, Lepidium, Lindernia, Papaver, Portlaca, PolygonumRanunculus, Rorippa, Rotala, Seneceio, Sesbania, Solanum, Sonchus,Taraxacum, Trifolium, Urtica and Xanthium is observed.

If the compounds of the formula (I) according to the invention areapplied to the soil surface prior to germination, then the weedseedlings are either prevented completely from emerging, or the weedsgrow until they have reached the seed leaf stage, but then their growthstops and, eventually, after three to four weeks have elapsed, they diecompletely.

If the active ingredients of the formula (I) are applied post-emergenceto the green parts of the plants, growth likewise stops drastically avery short time after the treatment and the weed plants remain at thegrowth stage at the time of application, or they die completely after acertain time, so that in this manner competition by the weeds, which isharmful to the crop plants, is eliminated very early on and in a lastingmanner.

Although the compounds of the formula (I) according to the inventionhave excellent herbicidal activity in respect of monocotyledonous anddicotyledonous weeds, crop plants of economically important crops, suchas, for example, wheat, barley, rye, rice, corn, sugarbeet, cotton,rapeseed and soybean, are only damaged negligibly, if at all. For thesereasons, the present compounds are very highly suitable for theselective control of undesired plant growth in agricultural usefulplantations. Moreover, the substances of the formula (I) according tothe invention have excellent growth regulatory properties in cropplants. They intervene in a plant's metabolism in a regulatory fashionand can thus be used for the targeted influencing of plant ingredientsand for facilitating harvesting, such as, for example, by triggeringdesiccation and stunted growth. Moreover, they are also suitable forgenerally controlling and inhibiting unwanted vegetative growth withoutdestroying the plants in the process. Inhibiting the vegetative growthplays a large role in many monocotyledonous and dicotyledonous crops,allowing lodging to be reduced or prevented completely.

On account of their herbicidal and plant growth regulatory properties,the active ingredients can also be used for controlling harmful plantsin crops of known plants or genetically modified plants which are yet tobe developed. As a rule, the transgenic plants are distinguished byparticular advantageous properties, for example by resistances tocertain pesticides, primarily certain herbicides, resistances to plantdiseases or pathogens of plant diseases, such as certain insects ormicroorganisms such as fungi, bacteria or viruses. Other particularproperties relate, for example, to the harvested material with respectto quantity, quality, storeability, composition and specificingredients. For example, transgenic plants with increased starchcontent or modified quality of the starch or those with a differentfatty acid composition of the harvested material are known. Furtherparticular properties can lie in a tolerance or resistance to abioticstress factors, for example heat, cold, drought, salt and ultravioletradiation.

Preference is given to using the compounds of the formula (I) accordingto the invention or salts thereof in economically important transgeniccrops of useful plants and ornamental plants, for example of cerealssuch as wheat, barley, rye, oats, millet, rice, manioc and corn, or elsecrops of sugarbeet, cotton, soybean, rapeseed, potatoes, tomatoes, peasand other vegetable varieties.

Preferably, the compounds of the formula (I) can be used as herbicidesin crops of useful plants which are resistant to, or have been renderedgenetically resistant to, the phytotoxic actions of the herbicides.

Conventional ways of producing new plants which have modified propertiescompared to existing plants consist, for example, in classic cultivationmethods and the generation of mutants. Alternatively, new plants withmodified properties can be produced using genetic engineering methods(see e.g. EP 0221044, EP 0131624).

For example, in several cases the following have been described:

-   -   genetic modifications of crop plants for the purpose of        modifying the starch synthesized in the plants (e.g. WO        92/011376, WO 92/014827, WO 91/019806),    -   transgenic crop plants which are resistant to certain herbicides        of the glufosinate type (cf. e.g. EP 0242236, EP 0242246) or of        the glyphosate type (WO 92/000377) or of the sulfonylurea type        (EP 0257993, U.S. Pat. No. 5,013,659),    -   transgenic crop plants, for example cotton, with the ability to        produce Bacillus thuringiensis toxins (Bt toxins) which make the        plants resistant to certain pests (EP 0142924, EP 0193259),    -   transgenic crop plants with a modified fatty acid composition        (WO 91/013972),    -   genetically modified crop plants with new ingredients or        secondary substances, e.g. new phytoalexins, which bring about        increased resistance to disease (EP 0309862, EP 0464461),    -   genetically modified plants with reduced photorespiration which        have higher yields and higher stress tolerance (EP 0305398),    -   transgenic crop plants which produce pharmaceutically or        diagnostically important proteins (“molecular pharming”),    -   transgenic crop plants distinguished by higher yields or better        quality,    -   transgenic crop plants distinguished by a combination e.g. of        the aforementioned new properties (“gene stacking”).

Numerous molecular biological techniques with which new transgenicplants with modified properties can be produced are known in principle;see e.g. I. Potrykus and G. Spangenberg (eds.) Gene Transfer to Plants,Springer Lab Manual (1995), Springer Verlag Berlin, Heidelberg orChristou, “Trends in Plant Science” 1 (1996) 423-431.

For such genetic manipulations, nucleic acid molecules which permit amutagenesis or a sequence modification by recombination of DNA sequencescan be introduced into plasmids. For example, with the help of standardmethods, it is possible to carry out base exchanges, to remove partsequences or to add natural or synthetic sequences. Adapters or linkersmay be added to the fragments in order to link the DNA fragments to oneanother, see e.g. Sambrook et al., 1989, Molecular Cloning, A LaboratoryManual, 2^(nd) edition, Cold Spring Harbor Laboratory Press, Cold SpringHarbor, N.Y.; or Winnacker “Gene and Klone [Genes and Clones]”, VCHWeinheim 2^(nd) edition 1996.

The preparation of plant cells with reduced activity of a gene productcan be achieved, for example, through the expression of at least onecorresponding antisense-RNA, a sense-RNA to achieve a cosuppressioneffect or the expression of at least one correspondingly constructedribozyme which specifically cleaves transcripts of the aforementionedgene product.

To this end, it is possible to use firstly DNA molecules which encompassthe entire coding sequence of a gene product including any flankingsequences which may be present, and also DNA molecules which onlyencompass parts of the coding sequence, it being necessary for theseparts to be long enough to bring about an antisense effect in the cells.Also possible is the use of DNA sequences which have a high degree ofhomology to the coding sequences of a gene product but are not entirelyidentical thereto.

During the expression of nucleic acid molecules in plants, thesynthesized protein can be localized in any compartment of the plantcell. However, in order to achieve localization in a certaincompartment, it is possible, for example, to link the coding region withDNA sequences which ensure localization in a certain compartment.Sequences of this type are known to the person skilled in the art (see,for example, Braun et al., EMBO J. 11 (1992), 3219-3227; Wolter et al.,Proc. Natl. Acad. Sci. USA 85 (1988), 846-850; Sonnewald et al., PlantJ. 1 (1991), 95-106). The expression of the nucleic acid molecules canalso take place in the organelles of the plant cells.

The transgenic plant cells can be regenerated by known techniques togive whole plants. In principle, the transgenic plants may be plants ofany desired plant species, i.e. both monocotyledonous and dicotyledonousplants.

Transgenic plants are thus obtainable which have modified properties asa result of overexpression, suppression or inhibition of homologous(=natural) genes or gene sequences, or expression of heterologous(=foreign) genes or gene sequences.

The compounds of the formula (I) according to the invention canpreferably be used in transgenic crops which are resistant to growthregulators, such as, for example, dicamba, or to herbicides whichinhibit essential plant enzymes, e.g. acetolactate synthases (ALS), EPSPsynthases, glutamine synthases (GS) or hydroxyphenylpyruvatedioxygenases (HPPD), or to herbicides from the group of sulfonylureas,glyphosates, glufosinates or benzoylisoxazoles and analogous activeingredients.

When using the active ingredients of the formula (I) according to theinvention in transgenic crops, besides the effects against harmfulplants that are observed in other crops, effects often arise which arespecific to the application in the particular transgenic crop, forexample a modified or specifically expanded weed spectrum which can becontrolled, modified application rates which can be used for theapplication, preferably good combinability with the herbicides againstwhich the transgenic crop is resistant, and also influencing of growthand yield of the transgenic crop plants.

The invention therefore also provides the use of the compounds of theformula (I) according to the invention as herbicides for controllingharmful plants in transgenic crop plants.

The compounds of the formula (I) can be formulated in different waysdepending on which biological and/or chemical-physical parameters areprescribed. Suitable formulation options are, for example: spray powders(WP), water-soluble powders (SP), water-soluble concentrates,emulsifiable concentrates (EC), emulsions (EW), such as oil-in-water andwater-in-oil emulsions, sprayable solutions, suspension concentrates(SC), dispersions based on oil or water, oil-miscible solutions, capsulesuspensions (CS), dusting agents (DP), seed dressings, granules forscattering and soil application, granules (GR) in the form ofmicrogranules, spray granules, coated granules and adsorption granules,water-dispersible granules (WG), water-soluble granules (SG), ULVformulations, microcapsules and waxes.

These individual formulation types are known in principle and aredescribed, for example, in: Winnacker-Küchler, “Chemische Technologie[Chemical Technology]”, Volume 7, C. Hanser Verlag Munich, 4^(th)edition 1986; Wade van Valkenburg, “Pesticide Formulations”, MarcelDekker, N.Y., 1973; K. Martens, “Spray Drying” Handbook, 3rd Ed. 1979,G. Goodwin Ltd. London.

The necessary formulation auxiliaries such as inert materials,surfactants, solvents and further additives are likewise known and aredescribed, for example, in: Watkins, “Handbook of Insecticide DustDiluents and Carriers”, 2nd Ed., Darland Books, Caldwell N. J., H. v.Olphen, “Introduction to Clay Colloid Chemistry”, 2nd Ed., J. Wiley &Sons, N.Y.; C. Marsden, “Solvents Guide”, 2nd Ed., Interscience, N.Y.1963; McCutcheon's “Detergents and Emulsifiers Annual”, MC Publ. Corp.,Ridgewood N.J.; Sisley and Wood, “Encyclopedia of Surface ActiveAgents”, Chem. Publ. Co. Inc., N.Y. 1964; Schönfeldt,“Grenzflächenaktive Äthylenoxidaddukte [Surface-active ethylene oxideadducts]”, Wiss. Verlagsgesell., Stuttgart 1976; Winnacker-Küchler,“Chemische Technologie [Chemical Technology]”, Volume 7, C. HanserVerlag Munich, 4^(th) edition, 1986.

On the basis of these formulations, it is also possible to preparecombinations with other pesticidally active substances, such as, forexample, insecticides, acaricides, herbicides, fungicides, and also withsafeners, fertilizers and/or growth regulators, e.g. in the form of aready mix or as tank mix.

Spray powders are preparations which can be dispersed uniformly in waterand which comprise, besides the active ingredient, apart from a diluentor inert substance, also surfactants of ionic and/or nonionic type(wetting agents, dispersants), e.g. polyoxyethylated alkylphenols,polyoxyethylated fatty alcohols, polyoxyethylated fatty amines, fattyalcohol polyglycol ether sulfates, alkanesulfonates,alkylbenzenesulfonates, sodium lignosulfonate, sodium2,2′-dinaphthylmethane-6,6′-disulfonate, sodiumdibutylnaphthalenesulfonate and also sodium oleoylmethyltaurate. Toprepare the spray powders, the herbicidal active ingredients are finelyground for example in customary apparatus such as hammer mills, blowingmills and air-jet mills and are mixed simultaneously or subsequentlywith the formulation auxiliaries.

Emulsifiable concentrates are prepared by dissolving the activeingredient in an organic solvent, e.g. butanol, cyclohexanone,dimethylformamide, xylene or else higher-boiling aromatics orhydrocarbons or mixtures of the organic solvents with the addition ofone or more surfactants of an ionic and/or nonionic type (emulsifiers).Emulsifiers which can be used are, for example: alkylarylsulfoniccalcium salts, such as Ca dodecylbenzenesulfonate, or nonionicemulsifiers, such as fatty acid polyglycol esters, alkylarylpolyglycolethers, fatty alcohol polyglycol ethers, propylene oxide-ethylene oxidecondensation products, alkyl polyethers, sorbitan esters, such assorbitan fatty acid esters, or polyoxyethylene sorbitan esters, such as,for example, polyoxyethylene sorbitan fatty acid esters.

Dusting agents are obtained by grinding the active ingredient withfinely divided solid substances, for example talc, natural clays, suchas kaolin, bentonite or pyrophyllite, or diatomaceous earth.

Suspension concentrates may be water-based or oil-based. They can beproduced, for example, by wet grinding by means of standard commercialbead mills and if appropriate addition of surfactants, as have forexample already been listed above in connection with the other types offormulation.

Emulsions, e.g. oil-in-water emulsions (EW), can be prepared, forexample, by means of stirrers, colloid mills and/or static mixers usingaqueous organic solvents and if appropriate surfactants, as have forexample already been listed above in connection with the other types offormulation.

Granules can be prepared either by atomizing the active ingredient ontogranulated inert material that is capable of adsorption or by applyingactive ingredient concentrates by means of adhesives, e.g. polyvinylalcohol, sodium polyacrylate or else mineral oils, onto the surface ofcarrier substances such as sand, kaolinites or of granulated inertmaterial. Suitable active ingredients can also be granulated in themanner customary for producing fertilizer granules—if desired in amixture with fertilizers.

Water-dispersible granules are usually prepared by customary methodssuch as spray-drying, fluidized-bed granulation, pan granulation, mixingwith high-speed mixers and extrusion without solid inert material.

For the preparation of pan granules, fluidized-bed granules, extrudergranules and spray granules, see, for example, methods in “Spray-DryingHandbook” 3rd ed. 1979, G. Goodwin Ltd., London; J. E. Browning,“Agglomeration”, Chemical and Engineering 1967, pages 147 ff; “Perry'sChemical Engineer's Handbook”, 5th Ed., McGraw-Hill, New York 1973, pp.8-57.

For further details relating to the formulation of crop protectioncompositions, see, for example, G. C. Klingman, “Weed Control as aScience”, John Wiley and Sons, Inc., New York, 1961, pages 81-96 and J.D. Freyer, S. A. Evans, “Weed Control Handbook”, 5th Ed., BlackwellScientific Publications, Oxford, 1968, pages 101-103.

The agrochemical preparations comprise generally 0.1 to 99% by weight,in particular 0.1 to 95% by weight, of active ingredient of the formula(I).

In spray powders, the active ingredient concentration is, for example,about 10 to 90% by weight, the remainder to 100% by weight consists ofcustomary formulation constituents. In the case of emulsifiableconcentrates, the active ingredient concentration can be about 1 to 90,preferably 5 to 80% by weight. Dust-like formulations comprise 1 to 30%by weight of active ingredient, preferably in most cases 5 to 20% byweight of active ingredient, sprayable solutions comprise about 0.05 to80, preferably 2 to 50% by weight of active ingredient. In the case ofwater-dispersible granules, the active ingredient content depends partlyon whether the active compound is present in liquid or solid form andwhich granulation auxiliaries, fillers etc. are used. In the case of thewater-dispersible granules, the content of active ingredient is, forexample, between 1 and 95% by weight, preferably between 10 and 80% byweight.

In addition, the specified active ingredient formulations optionallycomprise the adhesives, wetting agents, dispersants, emulsifiers,penetration agents, preservatives, antifreezes and solvents, fillers,carriers and colorants, antifoams, evaporation inhibitors and agentswhich influence the pH and the viscosity that are customary in eachcase.

The compounds of the formula (I) or their salts can be used as such orcombined in the form of their preparations (formulations) with otherpesticidally active substances, such as, for example, insecticides,acaricides, nematicides, herbicides, fungicides, safeners, fertilizersand/or growth regulators.

Combination partners which can be used for the compounds according tothe invention in mixture formulations or in the tank mix are, forexample, known active ingredients which are based on an inhibition of,for example, acetolactate synthase, acetyl-coenzyme-A-carboxylase,cellulose synthase, enolpyruvylshikimate-3-phosphate synthase, glutaminesynthetase, p-hydroxyphenylpyruvate dioxygenase, phytoene desaturase,photosystem I, photosystem II, protoporphyrinogen oxidase, as described,for example, in Weed Research 26 (1986) 441-445 or “The PesticideManual”, 13th edition, The British Crop Protection Council and the RoyalSoc. of Chemistry, 2003 and literature cited therein. Known herbicidesor plant growth regulators which can be combined with the compoundsaccording to the invention are, for example, the following activeingredients (the compounds are designated either with the “common name”in accordance with the International Organization for Standardization(ISO) or with the chemical name or with the code number) and alwaysencompass all of the application forms such as acids, salts, esters andisomers such as stereoisomers and optical isomers. Here, by way ofexample, one and sometimes also more application forms are specified:

acetochlor, acibenzolar, acibenzolar-S-methyl, acifluorfen,acifluorfen-sodium, aclonifen, alachlor, allidochlor, alloxydim,alloxydim-sodium, ametryn, amicarbazone, amidochlor, amidosulfuron,aminopyralid, amitrole, ammonium sulfamate, ancymidol, anilofos, asulam,atrazine, azafenidin, azimsulfuron, aziprotryn, BAH-043, BAS-140H,BAS-693H, BAS-714H, BAS-762H, BAS-776H, BAS-800H, beflubutamid,benazolin, benazolin-ethyl, bencarbazone, benfluralin, benfuresate,bensulide, bensulfuron-methyl, bentazone, benzfendizone, benzobicyclon,benzofenap, benzofluor, benzoylprop, bifenox, bilanafos,bilanafos-sodium, bispyribac, bispyribac-sodium, bromacil, bromobutide,bromofenoxim, bromoxynil, bromuron, buminafos, busoxinone, butachlor,butafenacil, butamifos, butenachlor, butralin, butroxydim, butylate,cafenstrole, carbetamide, carfentrazone, carfentrazone-ethyl,chlomethoxyfen, chloramben, chlorazifop, chlorazifop-butyl,chlorbromuron, chlorbufam, chlorfenac, chlorfenac-sodium, chlorfenprop,chlorflurenol, chlorflurenol-methyl, chloridazon, chlorimuron,chlorimuron-ethyl, chlormequat chloride, chlornitrofen, chlorophthalim,chlorthal-dimethyl, chlorotoluron, chlorsulfuron, cinidon,cinidon-ethyl, cinmethylin, cinosulfuron, clethodim, clodinafop,clodinafop-propargyl, clofencet, clomazone, clomeprop, cloprop,clopyralid, cloransulam, cloransulam-methyl, cumyluron, cyanamide,cyanazine, cyclanilide, cycloate, cyclosulfamuron, cycloxydim, cycluron,cyhalofop, cyhalofop-butyl, cyperquat, cyprazine, cyprazole, 2,4-D,2,4-DB, daimuron/dymron, dalapon, daminozide, dazomet, n-decanol,desmedipham, desmetryn, detosyl-pyrazolate (DTP), diallate, dicamba,dichlobenil, dichlorprop, dichlorprop-P, diclofop, diclofop-methyl,diclofop-P-methyl, diclosulam, diethatyl, diethatyl-ethyl, difenoxuron,difenzoquat, diflufenican, diflufenzopyr, diflufenzopyr-sodium,dimefuron, dikegulac-sodium, dimefuron, dimepiperate, dimethachlor,dimethametryn, dimethenamid, dimethenamid-P, dimethipin,dimetrasulfuron, dinitramine, dinoseb, dinoterb, diphenamid,dipropetryn, diquat, diquat-dibromide, dithiopyr, diuron, DNOC,eglinazine-ethyl, endothal, EPTC, esprocarb, ethalfluralin,ethametsulfuron-methyl, ethephon, ethidimuron, ethiozin, ethofumesate,ethoxyfen, ethoxyfen-ethyl, ethoxysulfuron, etobenzanid, F-5331, i.e.N-[2-chloro-4-fluoro-5[4-(3-fluoropropyl)-4,5-dihydro-5-oxo-1H-tetrazol-1-yl]phenyl]-ethanesulfonamide,fenoprop, fenoxaprop, fenoxaprop-P, fenoxaprop-ethyl,fenoxaprop-P-ethyl, fentrazamide, fenuron, flamprop,flamprop-M-isopropyl, flamprop-M-methyl, flazasulfuron, florasulam,fluazifop, fluazifop-P, fluazifop-butyl, fluazifop-P-butyl, fluazolate,flucarbazone, flucarbazone-sodium, flucetosulfuron, fluchloralin,flufenacet (thiafluamide), flufenpyr, flufenpyr-ethyl, flumetralin,flumetsulam, flumiclorac, flumiclorac-pentyl, flumioxazin, flumipropyn,fluometuron, fluorodifen, fluoroglycofen, fluoroglycofen-ethyl,flupoxam, flupropacil, flupropanate, flupyrsulfuron,flupyrsulfuron-methyl-sodium, flurenol, flurenol-butyl, fluridone,fluorochloridone, fluoroxypyr, fluoroxypyr-meptyl, flurprimidol,flurtamone, fluthiacet, fluthiacet-methyl, fluthiamide, fomesafen,foramsulfuron, forchlorfenuron, fosamine, furyloxyfen, gibberellic acid,glufosinate, L-glufosinate, L-glufosinate-ammonium,glufosinate-ammonium, glyphosate, glyphosate-isopropylammonium, H-9201,halosafen, halosulfuron, halosulfuron-methyl, haloxyfop, haloxyfop-P,haloxyfop-ethoxyethyl, haloxyfop-P-ethoxyethyl, haloxyfop-methyl,haloxyfop-P-methyl, hexazinone, HNPC-9908, HOK-201, HW-02,imazamethabenz, imazamethabenz-methyl, imazamox, imazapic, imazapyr,imazaquin, imazethapyr, imazosulfuron, inabenfide, indanofan, indoleacetic acid (IAA), 4-indol-3-ylbuttyric acid (IBA), iodosulfuron,iodosulfuron-methyl-sodium, ioxynil, isocarbamid, isopropalin,isoproturon, isouron, isoxaben, isoxachlortole, isoxaflutole,isoxapyrifop, IDH-100, KUH-043, KUH-071, karbutilate, ketospiradox,lactofen, lenacil, linuron, maleic hydrazide, MCPA, MCPB, MCPB-methyl,-ethyl and -sodium, mecoprop, mecoprop-sodium, mecoprop-butotyl,mecoprop-P-butotyl, mecoprop-P-dimethylammonium,mecoprop-P-2-ethylhexyl, mecoprop-P-potassium, mefenacet, mefluidide,mepiquat chloride, mesosulfuron, mesosulfuron-methyl, mesotrione,methabenzthiazuron, metam, metamifop, metamitron, metazachlor,methazole, methoxyphenone, methyldymron, 1-methylcyclopropene, methylisothiocyanate, metobenzuron, metobromuron, metolachlor, S-metolachlor,metosulam, metoxuron, metribuzin, metsulfuron, metsulfuron-methyl,molinate, monalide, monocarbamide, monocarbamide dihydrogensulfate,monolinuron, monosulfuron, monuron, MT 128, MT-5950, i.e.N-[3-chloro-4-(1-methylethyl)phenyl]-2-methylpentanamide, NGGC-011,naproanilide, napropamide, naptalam, NC-310, i.e.4-(2,4-dichlorobenzoyl)-1-methyl-5-benzyloxypyrazole, neburon,nicosulfuron, nipyraclofen, nitralin, nitrofen, nitrophenolat-sodium(isomer mixture), nitrofluorfen, nonanoic acid, norflurazon, orbencarb,orthosulfamuron, oryzalin, oxadiargyl, oxadiazon, oxasulfuron,oxaziclomefone, oxyfluorfen, paclobutrazol, paraquat, paraquatdichloride, pelargonic acid (nonanoic acid), pendimethalin, pendralin,penoxsulam, pentanochlor, pentoxazone, perfluidone, pethoxamid,phenisopham, phenmedipham, phenmedipham-ethyl, picloram, picolinafen,pinoxaden, piperophos, pirifenop, pirifenop-butyl, pretilachlor,primisulfuron, primisulfuron-methyl, probenazole, profluazol,procyazine, prodiamine, prifluraline, profoxydim, prohexadione,prohexadione-calcium, prohydrojasmone, prometon, prometryn, propachlor,propanil, propaquizafop, propazine, propham, propisochlor,propoxycarbazone, propoxycarbazone-sodium, propyzamide, prosulfalin,prosulfocarb, prosulfuron, prynachlor, pyraclonil, pyraflufen,pyraflufen-ethyl, pyrasulfotole, pyrazolynate (pyrazolate),pyrazosulfuron-ethyl, pyrazoxyfen, pyribambenz, pyribambenz-isopropyl,pyribenzoxim, pyributicarb, pyridafol, pyridate, pyriftalid,pyriminobac, pyriminobac-methyl, pyrimisulfan, pyrithiobac,pyrithiobac-sodium, pyroxasulfone, pyroxsulam, quinclorac, quinmerac,quinoclamine, quizalofop, quizalofop-ethyl, quizalofop-P,quizalofop-P-ethyl, quizalofop-P-tefuryl, rimsulfuron, secbumeton,sethoxydim, siduron, simazine, simetryn, SN-106279, sulcotrione,sulfallate (CDEC), sulfentrazone, sulfometuron, sulfometuron-methyl,sulfosate (glyphosate-trimesium), sulfosulfuron, SYN-523, SYP-249,SYP-298, SYP-300, tebutam, tebuthiuron, tecnazene, tefuryltrione,tembotrione, tepraloxydim, terbacil, terbucarb, terbuchlor, terbumeton,terbuthylazine, terbutryn, TH-547, thenylchlor, thiafluamide,thiazafluoron, thiazopyr, thidiazimin, thidiazuron, thiencarbazone,thiencarbazone-methyl, thifensulfuron, thifensulfuron-methyl,thiobencarb, tiocarbazil, topramezone, tralkoxydim, triallate,triasulfuron, triaziflam, triazofenamide, tribenuron, tribenuron-methyl,trichloroacetic acid (TCA), triclopyr, tridiphane, trietazine,trifloxysulfuron, trifloxysulfuron-sodium, trifluralin, triflusulfuron,triflusulfuron-methyl, trimeturon, trinexapac, trinexapac-ethyl,tritosulfuron, tsitodef, uniconazole, uniconazole-P, vernolate, ZJ-0166,ZJ-0270, ZJ-0543, ZJ-0862 and the following compounds

Of particular interest is the selective control of harmful plants incrops of useful plants and ornamental plants. Although the compounds ofthe formula (I) according to the invention already have very good toadequate selectivity in many crops, it is in principle possible, in somecrops and primarily also in the case of mixtures with other herbicideswhich are less selective, for phytotoxicities on the crop plants tooccur. In this connection, combinations of compounds of the formula (I)according to the invention are of particular interest which comprise thecompounds of the formula (I) or their combinations with other herbicidesor pesticides and safeners. The safeners which are used in anantidotically effective content reduce the phytotoxic side-effects ofthe herbicides/pesticides used, e.g. in economically important cropssuch as cereals (wheat, barley, rye, corn, rice, millet), sugarbeet,sugarcane, rapeseed, cotton and soybean, preferably cereals.

The safeners are preferably selected from the group consisting of:

S1) compounds of the formula (S1),

where the symbols and indices have the following meanings:

-   n_(A) is a natural number from 0 to 5, preferably 0 to 3;-   R_(A) ¹ is halogen, (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy, nitro or    (C₁-C₄)-haloalkyl;-   W_(A) is an unsubstituted or substituted divalent heterocyclic    radical from the group of the partially unsaturated or aromatic    five-ring heterocycles having 1 to 3 heteroring atoms from the group    consisting of N and O, where at least one N atom and at most one O    atom is present in the ring, preferably a radical from the group    (W_(A) ¹) to (W_(A) ⁴),

-   m_(A) is 0 or 1;-   R_(A) ² is OR_(A) ³, SR_(A) ³ or NR_(A) ³R_(A) ⁴ or a saturated or    unsaturated 3- to 7-membered heterocycle with at least one N atom    and up to 3 heteroatoms, preferably from the group consisting of O    and S, which is bonded to the carbonyl group in S1) via the N atom    and is unsubstituted or substituted by radicals from the group    consisting of (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy or optionally    substituted phenyl, preferably a radical of the formula OR_(A) ³, NH    R_(A) ⁴ or N(CH₃)₂, in particular of the formula OR_(A) ³;-   R_(A) ³ is hydrogen or an unsubstituted or substituted aliphatic    hydrocarbon radical, preferably having in total 1 to 18 carbon    atoms;-   R_(A) ⁴ is hydrogen, (C₁-C₆)-alkyl, (C₁-C₆)-alkoxy or substituted or    unsubstituted phenyl;-   R_(A) ⁵ is H, (C₁-C₈)-alkyl, (C₁-C₈)-haloalkyl,    (C₁-C₄)-alkoxy-(C₁-C₈)-alkyl, cyano or COOR_(A) ⁹, in which R_(A) ⁹    is hydrogen, (C₁-C₈)-alkyl, (C₁-C₈)-haloalkyl,    (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl, (C₁-C₆)-hydroxyalkyl,    (C₃-C₁₂)-cycloalkyl or tri-(C₁-C₄)-alkylsilyl;-   R_(A) ⁶, R_(A) ⁷, R_(A) ⁸ are identical or different, hydrogen,    (C₁-C₈)-alkyl, (C₁-C₈)-haloalkyl, (C₃-C₁₂)-cycloalkyl or substituted    or unsubstituted phenyl;    preferably:-   a) compounds of the dichlorophenylpyrazoline-3-carboxylic acid type    (S1^(a)), preferably compounds such as    1-(2,4-dichlorophenyl)-5-(ethoxycarbonyl)-5-methyl-2-pyrazoline-3-carboxylic    acid, ethyl    1-(2,4-dichlorophenyl)-5-(ethoxycarbonyl)-5-methyl-2-pyrazoline-3-carboxylate    (S1-1) (“mefenpyr-diethyl”), and related compounds, as described in    WO-A-91/07874;-   b) derivatives of dichlorophenylpyrazolecarboxylic acid (S1^(b)),    preferably compounds such as ethyl    1-(2,4-dichlorophenyl)-5-methylpyrazole-3-carboxylate (S1-2), ethyl    1-(2,4-dichlorophenyl)-5-isopropylpyrazole-3-carboxylate (S1-3),    ethyl    1-(2,4-dichlorophenyl)-5-(1,1-dimethylethyl)pyrazole-3-carboxylate    (S1-4) and related compounds, as described in EP-A-333 131 and    EP-A-269 806;-   c) derivatives of 1,5-diphenylpyrazole-3-carboxylic acid (S1^(c)),    preferably compounds such as ethyl    1-(2,4-dichlorophenyl)-5-phenylpyrazole-3-carboxylate (S1-5), methyl    1-(2-chlorophenyl)-5-phenylpyrazole-3-carboxylate (S1-6) and related    compounds, as described, for example, in EP-A-268554;-   d) compounds of the triazolecarboxylic acid type (S1^(d)),    preferably compounds such as fenchlorazole(-ethyl), i.e. ethyl    1-(2,4-dichlorophenyl)-5-trichloromethyl-(1H)-1,2,4-triazole-3-carboxylate    (S1-7), and related compounds, as described in EP-A-174 562 and    EP-A-346 620;-   e) compounds of the 5-benzyl- or 5-phenyl-2-isoxazoline-3-carboxylic    acid type or of the 5,5-diphenyl-2-isoxazoline-3-carboxylic acid    type (S1^(e)), preferably compounds such as ethyl    5-(2,4-dichlorobenzyl)-2-isoxazoline-3-carboxylate (S1-8) or ethyl    5-phenyl-2-isoxazoline-3-carboxylate (S1-9) and related compounds,    as described in WO-A-91/08202, or    5,5-diphenyl-2-isoxazoline-carboxylic acid (S1-10) or ethyl    5,5-diphenyl-2-isoxazoline-carboxylate (S1-11) (“isoxadifen-ethyl”)    or n-propyl 5,5-diphenyl-2-isoxazoline-carboxylate (S1-12) or of the    ethyl 5-(4-fluorophenyl)-5-phenyl-2-isoxazoline-3-carboxylate type    (S1-13), as described in the patent application WO-A-95/07897.-   S2) Quinoline derivatives of the formula (S2),

where the symbols and indices have the following meanings:

-   R_(B) ¹ is halogen, (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy, nitro or    (C₁-C₄)-haloalkyl;-   n_(B) is a natural number from 0 to 5, preferably 0 to 3;-   R_(B) ² is OR_(B) ³, SR_(B) ³ or NR_(B) ³R_(B) ⁴ or a saturated or    unsaturated 3- to 7-membered heterocycle having at least one N atom    and up to 3 heteroatoms, preferably from the group consisting of O    and S, which is joined to the carbonyl group in (S2) via the N atom    and is unsubstituted or substituted by radicals from the group    consisting of (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy or optionally    substituted phenyl, preferably a radical of the formula OR_(B) ³,    NHR_(B) ⁴ or N(CH₃)₂, in particular of the formula OR_(B) ³;-   R_(B) ³ is hydrogen or an unsubstituted or substituted aliphatic    hydrocarbon radical, preferably having in total 1 to 18 carbon    atoms;-   R_(B) ⁴ is hydrogen, (C₁-C₆)-alkyl, (C₁-C₆)-alkoxy or substituted or    unsubstituted phenyl;-   T_(B) is a (C₁ or C₂)-alkanediyl chain which is unsubstituted or    substituted by one or two (C₁-C₄)-alkyl radicals or by    [(C₁-C₃)-alkoxy]carbonyl;    preferably:-   a) compounds of the 8-quinolinoxy acetic acid type (S2^(a)),    preferably 1-methylhexyl (5-chloro-8-quinolinoxy)acetate    (“cloquintocet-mexyl”) (S2-1),    -   1,3-dimethylbut-1-yl (5-chloro-8-quinolinoxy)acetate (S2-2),    -   4-allyloxybutyl (5-chloro-8-quinolinoxy)acetate (S2-3),    -   1-allyloxyprop-2-yl (5-chloro-8-quinolinoxy)acetate (S2-4),    -   ethyl (5-chloro-8-quinolinoxy)acetate (S2-5),    -   methyl (5-chloro-8-quinolinoxy)acetate (S2-6),    -   allyl (5-chloro-8-quinolinoxy)acetate (S2-7),    -   2-(2-propylideneiminoxy)-1-ethyl (5-chloro-8-quinolinoxy)acetate        (S2-8),    -   2-oxoprop-1-yl (5-chloro-8-quinolinoxy)acetate (S2-9) and        related compounds,    -   as described in EP-A-86 750, EP-A-94 349 and EP-A-191 736 or        EP-A-0 492 366, and also (5-chloro-8-quinolinoxy)acetic acid        (S2-10), its hydrates and salts, for example its lithium,        sodium, potassium, calcium, magnesium, aluminum, iron, ammonium,        quaternary ammonium, sulfonium or phosphonium salts, as        described in WO-A-2002/34048;-   b) compounds of the (5-chloro-8-quinolinoxy)malonic acid type    (S2^(b)), preferably compounds such as diethyl    (5-chloro-8-quinolinoxy)malonate, diallyl    (5-chloro-8-quinolinoxy)malonate, methyl ethyl    (5-chloro-8-quinolinoxy)-malonate and related compounds, as    described in EP-A-0 582 198.-   S3) Compounds of the formula (S3)

where the symbols and indices have the following meanings:

-   R_(C) ¹ is (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₂-C₄)-alkenyl,    (C₂-C₄)-haloalkenyl, (C₃-C₇)-cycloalkyl, preferably dichloromethyl;-   R_(C) ², R_(C) ³ are identical or different, hydrogen,    (C₁-C₄)-alkyl, (C₂-C₄)-alkenyl, (C₂-C₄)-alkynyl, (C₁-C₄)-haloalkyl,    (C₂-C₄)-haloalkenyl, (C₁-C₄)-alkylcarbamoyl-(C₁-C₄)-alkyl,    (C₂-C₄)-alkenylcarbamoyl-(C₁-C₄)-alkyl,    (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl, dioxolanyl-(C₁-C₄)-alkyl, thiazolyl,    furyl, furylalkyl, thienyl, piperidyl, substituted or unsubstituted    phenyl, or R_(C) ² and R_(C) ³ form together a substituted or    unsubstituted heterocyclic ring, preferably an oxazolidine,    thiazolidine, piperidine, morpholine, hexahydropyrimidine or    benzoxazine ring;    preferably:    -   active ingredients of the dichloroacetamide type, which are        often used as pre-emergence safeners (soil-acting safeners),        such as, for example,    -   “dichlormid” (N,N-diallyl-2,2-dichloroacetamide) (S3-1),    -   “R-29148” (3-dichloroacetyl-2,2,5-trimethyl-1,3-oxazolidine)        from Stauffer (S3-2),    -   “R-28725” (3-dichloroacetyl-2,2-dimethyl-1,3-oxazolidine) from        Stauffer (S3-3),    -   “benoxacor”        (4-dichloroacetyl-3,4-dihydro-3-methyl-2H-1,4-benzoxazine)        (S3-4),    -   “PPG-1292”        (N-allyl-N-[(1,3-dioxolan-2-yl)methyl]dichloroacetamide) from        PPG Industries (S3-5),    -   “DKA-24”        (N-allyl-N-[(allylaminocarbonyl)methyl]dichloroacetamide) from        Sagro-Chem (S3-6),    -   “AD-67” or “MON 4660”        (3-dichloroacetyl-1-oxa-3-azaspiro[4,5]decane) from Nitrokemia        or Monsanto (S3-7),    -   “TI-35” (1-dichloroacetylazepane) from TRI-Chemical RT (S3-8),    -   “diclonon” (dicyclonone) or “BAS145138” or “LAB145138” (S3-9)        ((RS)-1-dichloroacetyl-3,3,8a-trimethylperhydropyrrolo[1,2-a]pyrimidin-6-one)        from BASF,    -   “furilazole” or “MON 13900”        ((RS)-3-dichloroacetyl-5-(2-furyl)-2,2-dimethyl-oxazolidine)        (S3-10); and also its (R)-isomer (S3-11).-   S4) N-Acylsulfonamides of the formula (S4) and their salts,

in which the symbols and indices have the following meanings:

-   X_(D) is CH or N;-   R_(D) ¹ is CO—NR_(D) ⁶R_(D) ⁶ or NHCO—R_(D) ⁷;-   R_(D) ² is halogen, (C₁-C₄)-haloalkyl, (C₁-C₄)-haloalkoxy, nitro,    (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy, (C₁-C₄)-alkylsulfonyl,    (C₁-C₄)-alkoxycarbonyl or (C₁-C₄)-alkylcarbonyl;-   R_(D) ³ is hydrogen, (C₁-C₄)-alkyl, (C₂-C₄)-alkenyl or    (C₂-C₄)-alkynyl;-   R_(D) ⁴ is halogen, nitro, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl,    (C₁-C₄)-haloalkoxy, (C₃-C₆)-cycloalkyl, phenyl, (C₁-C₄)-alkoxy,    cyano, (C₁-C₄)-alkylthio, (C₁-C₄)-alkyl-sulfinyl,    (C₁-C₄)-alkylsulfonyl, (C₁-C₄)-alkoxycarbonyl or    (C₁-C₄)-alkylcarbonyl;-   R_(D) ⁵ is hydrogen, (C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl,    (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, (C₅-C₆)-cycloalkenyl, phenyl or 3-    to 6-membered heterocyclyl comprising v_(D) heteroatoms from the    group consisting of nitrogen, oxygen and sulfur, where the seven    last-mentioned radicals are substituted by v_(D) substituents from    the group consisting of halogen, (C₁-C₆)-alkoxy, (C₁-C₆)-haloalkoxy,    (C₁-C₂)-alkylsulfinyl, (C₁-C₂)-alkylsulfonyl, (C₃-C₆)-cycloalkyl,    (C₁-C₄)-alkoxycarbonyl, (C₁-C₄)-alkylcarbonyl and phenyl and, in the    case of cyclic radicals, also (C₁-C₄)-alkyl and (C₁-C₄)-haloalkyl;-   R_(D) ⁶ is hydrogen, (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl or    (C₂-C₆)-alkynyl, where the three last-mentioned radicals are    substituted by v_(D) radicals from the group consisting of halogen,    hydroxy, (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy and (C₁-C₄)-alkylthio, or-   R_(D) ⁶ and R_(D) ⁶ together with the nitrogen atom carrying them    form a pyrrolidinyl or piperidinyl radical;-   R_(D) ⁷ is hydrogen, (C₁-C₄)-alkylamino, di(C₁-C₄)-alkylamino,    (C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl, where the 2 last-mentioned    radicals are substituted by V_(D) substituents from the group    consisting of halogen, (C₁-C₄)-alkoxy, (C₁-C₆)-haloalkoxy and    (C₁-C₄)-alkylthio and, in the case of cyclic radicals, also    (C₁-C₄)-alkyl and (C₁-C₄)-haloalkyl;-   n_(D) is 0, 1 or 2;-   m_(D) is 1 or 2;-   v_(D) is 0, 1, 2 or 3;    of which preference is given to compounds of the N-acylsulfonamide    type, for example of the following formula (S4^(a)), which are    known, for example, from WO-A-97/45016

in which

-   R_(D) ⁷ (C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl, where the 2    last-mentioned radicals are substituted by v_(D) substituents from    the group consisting of halogen, (C₁-C₄)-alkoxy, (C₁-C₆)-haloalkoxy    and (C₁-C₄)-alkylthio and, in the case of cyclic radicals, also    (C₁-C₄)-alkyl and (C₁-C₄)-haloalkyl;-   R_(D) ⁴ is halogen, (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy, CF₃;-   m_(D) is 1 or 2;-   v_(D) is 0, 1, 2 or 3;    and    -   acylsulfamoylbenzamides, e.g. of the following formula (S4^(b)),        which are known, for example, from WO-A-99/16744,

e.g. those in which

-   R_(D) ⁵=cyclopropyl and (R_(D) ⁴)=2-OMe (“cyprosulfamide”, S4-1),-   R_(D) ⁵=cyclopropyl and (R_(D) ⁴)=5-Cl-2-OMe (S4-2),-   R_(D) ⁵=ethyl and (R_(D) ⁴)=2-OMe (S4-3),-   R_(D) ⁵=isopropyl and (R_(D) ⁴)=5-Cl-2-OMe (S4-4) and-   R_(D) ⁵=isopropyl and (R_(D) ⁴)=2-OMe (S4-5),    and    -   compounds of the N-acylsulfamoylphenylurea type of the formula        (S4^(C)), which are known, for example, from EP-A-365484,

in which

-   -   R_(D) ⁸ and R_(D) ⁹, independently of one another, are hydrogen,        (C₁-C₈)-alkyl, (C₃-C₈)-cycloalkyl, (C₃-C₆)-alkenyl,        (C₃-C₆)-alkynyl,

-   R_(D) ⁴ is halogen, (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy, CF₃

-   m_(D) is 1 or 2;    for example

-   1-[4-(N-2-methoxybenzoylsulfamoyl)phenyl]-3-methylurea,

-   1-[4-(N-2-methoxybenzoylsulfamoyl)phenyl]-3,3-dimethylurea,

-   1-[4-(N-4,5-dimethylbenzoylsulfamoyl)phenyl]-3-methylurea.

-   S5) Active ingredients from the class of hydroxyaromatics and    aromatic-aliphatic carboxylic acid derivatives (S5), e.g. ethyl    3,4,5-triacetoxybenzoate, 3,5-dimethoxy-4-hydroxybenzoic acid,    3,5-dihydroxybenzoic acid, 4-hydroxysalicylic acid,    4-fluorosalicyclic acid, 2-hydroxycinnamic acid,    2,4-dichlorocinnamic acid, as described in WO-A-2004/084631,    WO-A-2005/015994, WO-A-2005/016001.

-   S6) Active ingredients from the class of the    1,2-dihydroquinoxalin-2-ones (S6), e.g.    1-methyl-3-(2-thienyl)-1,2-dihydroquinoxalin-2-one,    1-methyl-3-(2-thienyl)-1,2-dihydroquinoxaline-2-thione,    1-(2-aminoethyl)-3-(2-thienyl)-1,2-dihydro-quinoxalin-2-one    hydrochloride,    1-(2-methylsulfonylaminoethyl)-3-(2-thienyl)-1,2-dihydroquinoxalin-2-one,    as described in WO-A-2005/112630.

-   S7) Compounds of the formula (S7), as described in WO-A-1998/38856

in which the symbols and the indices have the following meanings:

-   R_(E) ¹, R_(E) ² independently of one another are halogen,    (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy, (C₁-C₄)-haloalkyl,    (C₁-C₄)-alkylamino, di(C₁-C₄)-alkylamino, nitro;-   A_(E) is COOR_(E) ³ or COSR_(E) ⁴-   R_(E) ³, R_(E) ⁴ independently of one another are hydrogen,    (C₁-C₄)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₄)-alkynyl, cyanoalkyl,    (C₁-C₄)-haloalkyl, phenyl, nitrophenyl, benzyl, halobenzyl,    pyridinylalkyl and alkylammonium,-   n_(E) ¹ is 0 or 1-   n_(E) ², n_(E) ³ independently of one another are 0, 1 or 2,    preferably:    -   diphenylmethoxyacetic acid,    -   ethyl diphenylmethoxyacetate,    -   methyl diphenylmethoxyacetate (CAS Reg. No. 41858-19-9) (S7-1).-   S8) Compounds of the formula (S8), as described in WO-A-98/27049

in which

-   X_(E) is CH or N,-   n_(F) if X_(F)═N, is an integer from 0 to 4 and if X_(F)═CH, is an    integer from 0 to 5,-   R_(F) ¹ is halogen, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl,    (C₁-C₄)-alkoxy, (C₁-C₄)-haloalkoxy, nitro, (C₁-C₄)-alkylthio,    (C₁-C₄)-alkylsulfonyl, (C₁-C₄)-alkoxycarbonyl, optionally    substituted phenyl, optionally substituted phenoxy,-   R_(F) ² is hydrogen or (C₁-C₄)-alkyl,-   R_(F) ³ is hydrogen, (C₁-C₈)-alkyl, (C₂-C₄)-alkenyl,    (C₂-C₄)-alkynyl, or aryl, where each of the aforementioned    C-containing radicals is unsubstituted or substituted by one or    more, preferably up to three, identical or different radicals from    the group consisting of halogen and alkoxy; or salts thereof,    preferably compounds in which-   X_(F) is CH,-   n_(F) is an integer from 0 to 2,-   R_(F) ¹ is halogen, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl,    (C₁-C₄)-alkoxy, (C₁-C₄)-haloalkoxy,-   R_(F) ² is hydrogen or (C₁-C₄)-alkyl,-   R_(F) ³ is hydrogen, (C₁-C₈)-alkyl, (C₂-C₄)-alkenyl,    (C₂-C₄)-alkynyl, or aryl, where each of the aforementioned    C-containing radicals is unsubstituted or substituted by one or    more, preferably up to three, identical or different radicals from    the group consisting of halogen and alkoxy, or salts thereof.-   S9) Active ingredients from the class of the    3-(5-tetrazolylcarbonyl)-2-quinolones (S9), e.g.    -   1,2-dihydro-4-hydroxy-1-ethyl-3-(5-tetrazolylcarbonyl)-2-quinolone        (CAS Reg. No. 219479-18-2),        1,2-dihydro-4-hydroxy-1-methyl-3-(5-tetrazolylcarbonyl)-2-quinolone        (CAS Reg. No. 95855-00-8), as described in WO-A-1999/000020.-   S10) Compounds of the formulae (S10^(a)) or (S10^(b)) as described    in WO-A-2007/023719 and WO-A-2007/023764

in which

-   R_(G) ¹ is halogen, (C₁-C₄)-alkyl, methoxy, nitro, cyano, CF₃, OCF₃-   Y_(G), Z_(G) independently of one another are O or S,-   n_(G) is an integer from 0 to 4,-   R_(G) ² is (C₁-C₁₆)-alkyl, (C₂-C₆)-alkenyl, (C₃-C₆)-cycloalkyl,    aryl; benzyl, halobenzyl,-   R_(G) ³ is hydrogen or (C₁-C₆)-alkyl.-   S11) Active ingredients of the oxyimino compound type (S11), which    are known as seed dressings, such as, for example,    -   “oxabetrinil”        ((Z)-1,3-dioxolan-2-ylmethoxyimino(phenyl)acetonitrile) (S11-1),    -   which is known as seed dressing safener for millet against        metolachlor damage,    -   “fluxofenim” (1-(4-chlorophenyl)-2,2,2-trifluoro-1-ethanone        OP-(1,3-dioxolan-2-ylmethyl)oxime) (S11-2), which is known as        seed dressing safener for millet against metolachlor damage, and    -   “cyometrinil” or “CGA-43089”        ((Z)-cyanomethoxyimino(phenyl)acetonitrile) (S11-3), which is        known as seed dressing safener for millet against metolachlor        damage.-   S12) Active ingredients from the class of the isothiochromanones    (S12), such as, for example, methyl    [(3-oxo-1H-2-benzothiopyran-4(3H)-ylidene)methoxy]acetate (CAS Reg.    No. 205121-04-6) (S12-1) and related compounds from WO-A-1998/13361.-   S13) One or more compounds from group (S13):    -   “naphthalic anhydride” (1,8-naphthalenedicarboxylic anhydride)        (S13-1), which is known as seed dressing safener for corn        against thiocarbamate herbicide damage,    -   “fenclorim” (4,6-dichloro-2-phenylpyrimidine) (S13-2), which is        known as safener for pretilachlor in sown rice,    -   “flurazole” (benzyl        2-chloro-4-trifluoromethyl-1,3-thiazole-5-carboxylate) (S13-3),        which is known as seed dressing safener for millet against        alachlor and metolachlor damage,    -   “CL 304415” (CAS Reg. No. 31541-57-8)        (4-carboxy-3,4-dihydro-2H-1-benzopyran-4-acetic acid) (S13-4)        from American Cyanamid, which is known as safener for corn        against imidazolinone damage,    -   “MG 191” (CAS Reg. No. 96420-72-3)        (2-dichloromethyl-2-methyl-1,3-dioxolane) (S13-5) from        Nitrokemia, which is known as safener for corn,    -   “MG-838” (CAS Reg. No. 133993-74-5) (2-propenyl        1-oxa-4-azaspiro[4.5]decane-4-carbodithioate) (S13-6) from        Nitrokemia,    -   “disulfoton” (O,O-diethyl S-2-ethylthioethyl phosphorodithioate)        (S13-7),    -   “dietholate” (O,O-diethylO-phenylphosphorothioate) (S13-8),    -   “mephenate” (4-chlorophenyl methylcarbamate) (S13-9).-   S14) Active ingredients which, besides a herbicidal effect against    harmful plants, also have a safener effect on crop plants such as    rice, such as, for example, “dimepiperate” or “MY-93”    (S-1-methyl-1-phenylethyl piperidine-1-carbothioate), which is known    as safener for rice against molinate herbicide damage,    -   “daimuron” or “SK 23”        (1-(1-methyl-1-phenylethyl)-3-p-tolylurea), which is known as        safener for rice against imazosulfuron herbicide damage,    -   “cumyluron”=“JC-940”        (3-(2-chlorophenylmethyl)-1-(1-methyl-1-phenyl-ethyl)urea, see        JP-A-60087254), which is known as safener for rice against some        herbicide damage,    -   “methoxyphenone” or “NK 049”        (3,3′-dimethyl-4-methoxybenzophenone), which is known as safener        for rice against some herbicide damage, “CSB”        (1-bromo-4-(chloromethylsulfonyl)benzene) from Kumiai, (CAS Reg.        No. 54091-06-4), which is known as safener against some        herbicide damage in rice.-   S15) Active ingredients which are primarily used as herbicides, but    also have safener effect on crop plants, for example    -   (2,4-dichlorophenoxy)acetic acid (2,4-D),    -   (4-chlorophenoxy)acetic acid,    -   (R,S)-2-(4-chloro-o-tolyloxy)propionic acid (mecoprop),    -   4-(2,4-dichlorophenoxy)butyric acid (2,4-DB),    -   (4-chloro-o-tolyloxy)acetic acid (MCPA),    -   4-(4-chloro-o-tolyloxy)butyric acid,    -   4-(4-chlorophenoxy)butyric acid,    -   3,6-dichloro-2-methoxybenzoic acid (dicamba),    -   1-(ethoxycarbonyl)ethyl 3,6-dichloro-2-methoxybenzoate        (lactidichlor-ethyl).

Some of the safeners are already known as herbicides and thus, besidesthe herbicidal effect in respect of harmful plants, at the same timealso develop a protective effect in respect of the crop plants.

The weight ratios of herbicide (mixture) to safener generally depend onthe application rate of herbicide and the effectiveness of theparticular safener and can vary within wide limits, for example in therange from 200:1 to 1:200, preferably 100:1 to 1:100, in particular 20:1to 1:20. The safeners can be formulated analogously to the compounds ofthe formula (I) or mixtures thereof with further herbicides/pesticidesand can be provided and applied as ready mix or tank mix with theherbicides.

For use, the formulations present in standard commercial form are, ifappropriate, diluted in the usual manner, e.g. in the case of spraypowders, emulsifiable concentrates, dispersions and water-dispersiblegranules by means of water. Dust-like preparations, soil and scattergranules, and also sprayable solutions are usually no longer dilutedwith further inert substances prior to use.

The required application rate of the compounds of the formula (I) variesinter alia with the external conditions such as temperature, humidity,the type of herbicide used. It can fluctuate within wide limits, e.g.between 0.001 and 10.0 kg/ha or more of active substance, but ispreferably between 0.005 and 5 kg/ha.

The present invention is illustrated in more detail by reference to theexamples below, although these do not limit the invention in any way.

A. Synthesis Examples Preparation Examples2-Amino-4-indanyl-1-amino-6-methylpyrimidine (Ex.: 1-4)

A mixture of 2.9 g (20 mmol) of 2-amino-4-chloro-6-methylpyrimidine, 2.9g (22 mmol) of 1-aminoindane and 4.1 g (30 mmol) of potassium carbonatein 30 ml of dimethylformamide is heated at 145° C. for 3 hours. Aftercooling, the reaction mixture is hydrolyzed, the aqueous mixture isextracted with methylene chloride, the separated-off organic phase isdried with sodium sulfate. After filtering off the drying agent andconcentrating the organic phase by evaporation, the crude mixture isseparated by means of column chromatographic separation using ethylacetate/methanol/triethylamine 90/10/1 as eluent. The2-amino-4-indanyl-1-amino-6-methylpyrimidine obtained in this way istaken up in ethyl acetate/heptane 2:8 and treated with activated carbon.After separating off the activated carbon and concentrating the solventby evaporation, 1 g of 2-amino-4-indanyl-1-amino-6-methylpyrimidine isobtained (glass-like solid, m.p: 53-54° C., 20% yield, 95% purity).

N4-[(1R,2S)-2,6-dimethyl-2,3-dihydro-1H-inden-1-yl]-6-(trifluoromethyl)pyrimidine-2,4-diamine(Ex.: 1-27)

A mixture of 0.3 g (1.5 mmol) of2-amino-4-chloro-6-trifluoromethylpyrimidine, 0.3 g (1.5 mmol) of(1R,2S)-2,6-dimethyl-2,3-dihydro-1H-inden-1-aminium chloride and 0.53 g(3.8 mmol) of potassium carbonate in 3 ml of dimethylformamide is heatedat 120° C. for 5 hours. After cooling, the reaction mixture is adsorbedon silica gel and purified by means of column chromatography using ethylacetate/heptane as eluent. Following concentration by evaporation, 0.24g of solidN4[(1R,2S)-2,6-dimethyl-2,3-dihydro-1H-inden-1-yl]-6-(trifluoromethyl)pyrimidine-2,4-diamineis obtained (44% yield, 90% purity).

33.4 g (0.186 mol) of 4-hydroxy-6-trifluoromethylpyrimidin-2-ylamine areadded in portions (in each case ca. 5 g) to a mixture of 85 ml ofphosphorus oxychloride and 47.5 ml of dimethylaniline and the mixture isheated at reflux until the added solid has dissolved. The mixture isthen heated at reflux for a further 90 minutes. After cooling, thereaction mixture is added to ice water while observing the safetyprecautions for phosphorus oxychloride. The aqueous phase is extractedwith methylene chloride, the organic phase is separated off and driedwith sodium sulfate, and the drying agent is filtered off. Followingconcentration by evaporation, 47.8 g of a crude mixture are obtained.Following column chromatographic separation with ethyl acetate/heptaneas eluent, 8.5 g of 4-chloro-6-trifluoromethylpyrimidin-2-ylamine wereobtained (solid, 22% yield, purity 95%).

5-Chloro-N-4-[(1R,2S)-2,6-dimethyl-2,3-dihydro-1H-inden-1-yl]-6-(trifluoro-methyl)pyrimidine-2,4-diamine(Ex.: 1-38)

A mixture of 0.10 g (0.43 mmol) of4,5-dichloro-6-(trifluoromethyl)pyrimidin-2-amine, 0.08 g (0.51 mmol) of(1R,2S)-2,6-dimethyl-2,3-dihydro-1H-inden-1-amine and 0.14 g (1.3 mmol)of potassium carbonate in 1 ml of dimethylacetamide as solvent is heatedat 125° C. for 30 minutes in a microwave appliance (Biotage Initiator,http://www.biotage.com/DynPage.aspx?id=22001). The crude mixture isabsorbed on silica gel and, following column chromatographic separation,0.089 g of5-chloro-N4-[(1R,2S)-2,6-dimethyl-2,3-dihydro-1H-inden-1-yl]-6-(trifluoromethyl)pyrimidin-2,4-diamineis obtained (solid, 55% yield, 95% purity).

2-Amino-4-phenyl-6-[(1R)-1,2,3,4-tetrahydronaphthalen-1-ylamino]pyrimidine-5-carbonitrile(Ex.: 1-53)

A mixture of 0.40 g (1.21 mmol) of2-amino-4-chloro-6-phenylpyrimidine-5-carbonitrile (crude mixture asprecursor, ca. 70% purity), 0.27 g (1.82 mmol) of(1R,2S)-2,6-dimethyl-2,3-dihydro-1H-inden-1-amine and 0.34 g (2.42 mmol)of potassium carbonate is heated in 1 ml of N-methylpyrrolidone assolvent at 150° C. for 60 minutes in a microwave appliance (BiotageInitiator, http://www.biotage.com/DynPage.aspx?id=22001). The crudemixture is absorbed on silica gel and, following column chromatographicseparation, 0.291 g of2-amino-4-phenyl-6-[(1R)-1,2,3,4-tetrahydronaphthalen-1-ylamino]pyrimidine-5-carbonitrileis obtained (solid, 67% yield, 95% purity).

6.6 g (31.1 mmol) of2-amino-6-oxo-4-phenyl-1,6-dihydropyrimidine-5-carbonitrile are added inportions (in each case ca. 1 g) to a mixture of 50 ml of phosphorusoxychloride and 0.5 ml of dimethylaniline and the mixture is heated atreflux until the added solid has dissolved. The mixture is then heatedat reflux for a further 90 minutes. After cooling, the reaction mixtureis added to ice water while observing the safety precautions forphosphorus oxychloride. The aqueous phase is extracted with methylenechloride, the organic phase is separated off and dried with sodiumsulfate, and the drying agent is filtered off. Following concentrationby evaporation, 3.2 g of2-amino-4-chloro-6-phenylpyrimidine-5-carbonitrile are obtained (solid,ca. 70% purity, contaminated with2-amino-6-oxo-4-phenyl-1,6-dihydropyrimidine-5-carbonitrile anddimethylaniline; the crude mixture can be used in the subsequent stagewithout further purification).

7.6 ml of (7.4 g, density 0.98 g/l, 41.2 mmol) of a commerciallyavailable 30% sodium methanolate solution are added dropwise to amixture of 80 ml of methanol, 5.5 g (34.5 mmol) of methylN-cyanobenzenecarboximidoate and 2.9 g (34.5 mmol) of cyanacetamide. Thereaction mixture is heated at reflux for 120 minutes, the mixture iscooled and concentrated by evaporation, and the residue which remains istaken up in water. The aqueous phase is then neutralized with conc.sulfuric acid and the precipitated solid is isolated. After drying, 6.78g of 2-amino-6-oxo-4-phenyl-1,6-dihydropyrimidine-5-carbonitrile areobtained (solid, ca. 95% purity).

N4-[(1R)-1,2,3,4-tetrahydronaphthalen-1-yl]-5-(trifluoromethyl)pyrimidine-2,4-diamine(Ex.: 1-60)

With stirring, 1.0 g of 2,4-dichloro-5-(trifluoromethyl)pyrimidine,Aldrich order no. 684864, is added to a methanolic ammonia solution (ca.8 mol of ammonia in methanol) cooled to ca. 5° C., the mixture is heatedto 25° C. and stirred for 2 hours at this temperature. The mixture isconcentrated by evaporation and added to water. After filtering off withsuction, 0.56 g of a mixture of4-amino-2-chloro-5-trifluoromethylpyrimidine (ca. 45%) and2-amino-4-chloro-5-trifluoromethylpyrimidine (ca. 45%) is obtained.

Then, a mixture of 0.25 g of the solid obtained above and 0.224 g (1.47mmol) of (R)-1,2,3,4-tetrahydro-1-naphthylamine and 0.35 g (2.53 mmol)of potassium carbonate in 1 ml N-methylpyrrolidone as solvent is heatedin a closed cell in a microwave appliance (Biotage Initiator,http://www.biotage.com/DynPage.aspx?id=22001) at 160° C. for 60 minutes.The crude mixture is absorbed on silica gel and, following separation bymeans of column chromatography, 0.190 g ofN4-[(1R)-1,2,3,4-tetrahydronaphthalen-1-yl]-5-(trifluoro-methyl)pyrimidine-2,4-diamine(wax-like, 95% purity) is obtained.

Chemicophysical data: Compound Description 1.4 solid, m.p.: 53-55° C.;1H-NMR (CDCl₃, 300 MHZ, δ in ppm): 1.85 (m, 1H, 1H from CH₂); 2.50 (m,1H, 1H from CH₂) 2.80 (m, 2H, CH₂); 5.10-5.50 (m, 4H, CH, NH, NH₂); 5.70(s, 1H, PYR-H); 7.15-7.30 (m, 4H, Ar—H) 1.17 solid, m.p.: 184-185° C.;;1H-NMR (CDCl₃, 300 MHZ, δ in ppm): 1.70-2.00 (m, 2 * CH₂); 2.20 (s, 3H,CH₃); 2.25 (s, 3H, CH₃); 2.50 (m, 2H, CH₂); 4.80-5.40 (m, 4H, CH, NH₂,NH); 6.10 (s, 1H, PYR-H); 6.95 (br, 2H, Ar—H) 1.18 solid, m.p.: 134-135°C.; 1H-NMR (CDCl₃, 300 MHZ, δ in ppm): 1.90 (m, 1H, 1H from CH₂); 2.60(m, 1H, 1H from CH₂) 2.90 (m, 2H, CH₂); 5.10-5.50 (m, 4H, CH, NH, NH₂);6.10 (s, 1H, PYR-H); 7.15-7.30 (m, 4H, Ar—H) 1.19 solid, m.p.: 167-168°C.; 1H-NMR (CDCl₃, 300 MHZ, δ in ppm): 1.90 (m, 1H, 1H from CH₂); 2.60(m, 1H, 1H from CH₂) 2.90 (m, 2H, CH₂); 3.70 (s, 3H, OCH₃); 4.95 (br,2H, NH₂); 5.50 (d, 1H, NH); 5.70 (dd, 1H, CH); 7.15-7.30 (m, 4H, Ar—H)1.24 solid, m.p.: 194-195° C.; 1H-NMR (CDCl₃, 300 MHZ, δ in ppm):1.70-2.00 (m, 2 * CH₂); 2.20 (s, 3H, CH₃); 2.30 (s, 3H, CH₃); 2.50 (m,2H, CH₂); 3.70 (s, 3H, OCH₃); 4.95 (br, 2H, NH₂); 5.30 (br, 1H, CH);5.50 (d, 1H, NH); 6.95 (br, 2H, Ar—H) 1.25 solid, m.p.: 140-142° C.;1H-NMR (CDCl₃, 300 MHZ, δ in ppm): 1.70-2.00 (m, 2 * CH₂); 2.20 (s, 3H,CH₃); 2.30 (s, 3H, CH₃); 2.35 (s, 3H, CH₃); 2.50 (m, 2H, CH₂); 5.15 (br,1H, CH); 5.30 (br, 2H, NH₂); 6.50 (d, 1H, NH); 6.95 (br, 2H, Ar—H) 1.26solid, m.p.: 156-158° C.; 1H-NMR (CDCl₃, 300 MHZ, δ in ppm): 1.90 (m,1H, 1H from CH₂); 2.00 (s, 3H, CH₃); 2.60 (m, 1H, 1H from CH₂) 2.90 (m,2H, CH₂); 4.80 (br, 2H, NH₂); 4.95 (d, 1H, NH); 5.75 (dd, 1H, CH);7.15-7.30 (m, 4H, Ar—H) 1.27 solid; logp (HCOOH): 2.77; 1H-NMR (CDCl₃,400 MHZ, δ in ppm): 1.25 (d, 3H, CH₃); 2.25 (m, 1H, 1H from CH₂); 2.30(s, 3H, CH₃); 2.35 (s, 3H, CH₃); 2.50 (dd, 1H, 1H from CH₂); 3.05 (dd,1H, CH); 4.40-6.40 (m, 4H, NH₂, NH, CH); 6.95-7.10 (m, 3H, Ar—H) 1.30solid; m.p.: 197.7° C.; logp (HCOOH): 1.39; 1H-NMR (DMSO, 400 MHZ, δ inppm): 1.20 (d, 3H, CH₃); 2.25 (m, 1H, 1H from CH₂); 2.30 (s, 3H, CH₃);2.30 (s, 3H, CH₃); 2.50 (dd, 1H, 1H from CH₂); 3.05 (dd, 1H, CH); 5.20(t, 1H, CH); 6.25 (br, 2H, NH₂); 6.40 (t, 1H, CF₂H); 6.90-7.10 (m, 3H,Ar—H); 7.50 (br, 1H, NH); 1.35 solid; logp (HCOOH): 1.18; 1H-NMR (CDCl₃,400 MHZ, δ in ppm): 1.85 (m, 3H, 1H from CH₂; CH₂); 2.05 (m, 1H, 1H fromCH₂); 2.80 (m, 2H, CH₂); 4.70-5.50 (m, 3H, CH, NH₂); 6.00 (br, 1H, NH);6.20 (t, 1H, CF₂H); 7.05-7.30 (m, 4H, Ar—H) 1.36 Wachsartig; logp(HCOOH): 1.08; 1H-NMR (CDCl₃, 400 MHZ, δ in ppm): 1.85 (m, 1H, 1H fromCH₂); 2.65 (m, 1H, 1H from CH₂) 2.80 und 2.95 (in each case m, 2H, 1Hfrom CH₂); 4.70-5.50 (m, 3H, CH, NH₂); 6.20 (br, 1H, NH); 6.20 (t, 1H,CF₂H); 7.15-7.30 (m, 4H, Ar—H) 1.38 solid; m.p.: 169.2° C.; logp(HCOOH): 3.98; 1H-NMR (CDCl₃, 400 MHZ, δ in ppm): 1.25 (d, 3H, CH₃);2.30 (m, 1H, 1H from CH₂); 2.30 (s, 3H, CH₃); 2.50 (dd, 1H, 1H fromCH₂); 3.10 (dd, 1H, CH); 4.95 (br, 2H, NH₂); 5.30 (t, 1H, CH); 5.70 (br,1H, NH); 6.95 (s, 1H, Ar—H); 7.05 (dd, 2H, Ar—H); 1.41 solid; logp(HCOOH): 3.27; 1H-NMR (CDCl₃, 400 MHZ, δ in ppm): 1.25 (d, 3H, CH₃);2.30 (m, 1H, 1H from CH₂); 2.30 (s, 3H, CH₃); 2.55 (dd, 1H, 1H fromCH₂); 3.10 (dd, 1H, CH); 3.75 (s, 3H, OCH₃); 5.30 (t, 1H, CH); 5.80 (br,2H, NH₂); 5.70 (br, 1H, NH); 6.95 (s, 1H, Ar—H); 7.05 (dd, 2H, Ar—H);1.42 wax-like; logp (HCOOH): 2.60; 1H-NMR (CDCl₃, 400 MHZ, δ in ppm):1.25 (d, 3H, CH₃); 2.25 (m, 1H, 1H from CH₂); 2.30 (s, 3H, CH₃); 2.50(m, 1H, 1H from CH₂); 3.00 (dd, 1H, CH); 4.70-5.00 (m, 4H, NH₂, NH, CH);5.90 (br, 1H, PYR-H); 6.95-7.10 (m, 3H, Ar—H); 1.43 wax-like; logp(HCOOH): 2.16; 1H-NMR (CDCl₃, 400 MHZ, δ in ppm): 1.85 (m, 3H, 3H fromCH₂); 2.05 (m, 1H, 1H from CH₂); 2.80 (m, 2H, CH); 4.70-5.00 (m, 4H,NH₂, NH, CH); 5.80 (br, 1H, PYR-H); 7.05-7.30 (m, 4H, Ar—H); 1.44wax-like; logp (HCOOH): 1.95; 1H-NMR (CDCl₃, 400 MHZ, δ in ppm): 1.85(m, 1H, 1H from CH₂); 2.60 (m, 1H, 1H from CH₂); 2.90 (m, 1H, 1H fromCH₂); 3.00 (m, 1H, 1H from CH₂); 4.70-5.00 (m, 4H, NH₂, NH, CH); 5.90(br, 1H, PYR-H); 7.15-7.30 (m, 4H, Ar—H); 1.45 wax-like; logp (HCOOH):2.87; 1H-NMR (CDCl₃, 400 MHZ, δ in ppm): 1.85 (m, 3H, 1H from CH₂; CH₂);2.05 (m, 1H, 1H from CH₂); 2.80 (m, 2H, CH₂); 4.80 (br, 2H, NH₂); 5.35(t, 1H, CH); 5.50 (br, 1H, NH); 7.05-7.30 (m, 4H, Ar—H) 1.47 wax-like;logp (HCOOH): 3.76; 1H-NMR (CDCl₃, 400 MHZ, δ in ppm): 1.85 (m, 3H, 3Hfrom CH₂); 2.05 (m, 1H, 1H from CH₂); 2.80 (m, 2H, CH); 4.95 (br, 2H,NH₂); 5.40 (br, 1H, CH); 5.80 (br, H, NH); 7.05-7.30 (m, 4H, Ar—H); 1.51solid; m.p.: 164-5° C.; logp (HCOOH): 3.27; 1H-NMR (CDCl₃, 400 MHZ, δ inppm): 1.25 (d, 3H, CH₃); 2.35 (m, 1H, 1H from CH₂); 2.35 (s, 3H, CH₃);2.55 (dd, 1H, 1H from CH₂); 3.10 (dd, 1H, CH); 5.25 (br, 2H, NH₂); 5.45(t, 1H, CH); 5.60 (br, 1H, NH); 6.95 (s, 1H, Ar—H); 7.05 (dd, 2H, Ar—H);7.50 (m, 3H, Ar—H); 7.90 (m, 2H, Ar—H); 1.53 solid; logp (HCOOH): 2.87;1H-NMR (CDCl₃, 400 MHZ, δ in ppm): 1.85 (m, 3H, 1H from CH₂; CH₂); 2.10(m, 1H, 1H from CH₂); 2.80 (m, 2H, CH₂); 5.25 (br, 2H, NH₂); 5.50 (t,1H, CH); 5.70 (br, 1H, NH); 7.10-7.30 (m, 4H, Ar—H); 7.50 (m, 3H, Ar—H);7.90 (m, 2H, Ar—H); 1.54 wax-like; logp (HCOOH): 1.71; 1H-NMR (CDCl₃,400 MHZ, δ in ppm): 1.25 (d, 3H, CH₃); 2.35 (m, 1H, 1H from CH₂); 2.35(s, 3H, CH₃); 2.40 (s, 3H, CH₃); 2.55 (dd, 1H, 1H from CH₂); 3.10 (dd,1H, CH); 5.10 (br, 2H, NH₂); 5.40 (br, 2H, CH, NH); 6.95 (s, 1H, Ar—H);7.05 (dd, 2H, Ar—H); 1.57 solid, m.p.: 144-145° C.; logp (HCOOH): 1.64;1H-NMR (CDCl₃, 400 MHZ, δ in ppm): 1.25 (d, 3H, CH₃); 2.35 (m, 1H, 1Hfrom CH₂); 2.35 (s, 3H, CH₃); 2.50 (dd, 1H, 1H from CH₂); 3.05 (dd, 1H,CH); 5.00 (br, 2H, NH₂); 5.20 (br, 1H, NH); 5.45 (t, 1H, CH); 6.95 (s,1H, Ar—H); 7.05 (dd, 2H, Ar—H); 8.15 (s, 1H, PYR-H) 1.58 solid; logp(HCOOH): 1.49; 1H-NMR (CDCl₃, 400 MHZ, δ in ppm): 1.85 (m, 3H, 3H fromCH₂); 2.10 (m, 1H, 1H from CH₂); 2.80 (m, 2H, CH); 4.95 (br, 2H, NH₂);5.20 (br, 1H, CH); 5.50 (br, H, NH); 7.05-7.30 (m, 4H, Ar—H); 8.05 (s,1H, PYR-H); 1.59 wax-like; logp (HCOOH): 1.16; 1H-NMR (CDCl₃, 400 MHZ, δin ppm): 1.85 (m, 3H, 1H from CH₂; CH₂); 2.10 (m, 1H, 1H from CH₂); 2.30(s, 3H, CH₃); 2.85 (m, 2H, CH₂); 5.25 (br, 2H, NH₂); 5.40 (br, 2H, NH,CH); 7.10-7.30 (m, 4H, Ar—H); 1.60 solid, m.p.: 120-121° C.; logp(HCOOH): 1.55; 1H-NMR (CDCl₃, 400 MHZ, δ in ppm): 1.25 (d, 3H, CH₃);2.35 (m, 1H, 1H from CH₂); 2.35 (s, 3H, CH₃); 2.40 (s, 3H, CH₃); 2.55(dd, 1H, 1H from CH₂); 3.10 (dd, 1H, CH); 5.00 (br, 2H, NH₂); 5.35 (t,1H, CH); 5.60 (br, 1H, NH); 6.95 (s, 1H, Ar—H); 7.05 (dd, 2H, Ar—H);1.62 wax-like; 1H-NMR (CDCl₃, 400 MHZ, δ in ppm): 1.85 (m, 3H, 1H fromCH₂; CH₂); 2.05 (m, 1H, 1H from CH₂); 2.35 (s, 3H, CH₃); 2.85 (m, 2H,CH₂); 4.70 (br, 2H, NH₂); 5.40 (m, 2H, NH, CH); 7.10-7.30 (m, 4H, Ar—H);1.63 solid, logp (HCOOH): 2.54; 1H-NMR (CDCl₃, 400 MHZ, δ in ppm): 1.25(d, 3H, CH₃); 2.35 (m, 1H, 1H from CH₂); 2.35 (s, 3H, CH₃); 2.50 (dd,1H, 1H from CH₂); 3.10 (dd, 1H, CH); 4.05 (s, 3H, OCH₃); 5.00-5.60 (n,4H, NH, CH, NH₂); 6.80 (br, 1H, PYR-H); 6.95 (s, 1H, Ar—H); 7.05 (dd,2H, Ar—H); 1.210 solid, m.p.: 168-169° C.; logp (HCOOH): 3.41; 1H-NMR(CDCl₃, 400 MHZ, δ in ppm): 1.90 (m, 1H, 1H from CH₂); 2.70 (m, 1H, 1Hfrom CH₂); 2.90 (m, 1H, 1H from CH₂); 3.05 (m, 1H, 1H from CH₂); 4.95(br, 2H, NH₂); 5.65 (br, 1H, CH); 5.75 (br, H, NH); 7.15-7.30 (m, 4H,Ar—H); 1.212 wax-like; logp (HCOOH): 1.64; 1H-NMR (CDCl₃, 400 MHZ, δ inppm): 1.20 (t, 3H, CH₃); 2.10 (m, 1H, 1H from CH₂); 2.25 (m, 1H, 1H fromCH₂); 2.55 (m, 2H, 2H from CH₂CH₃); 4.15 (m, 1H, 1H from CH₂O); 4.25 (m,1H, 1H from CH₂O); 5.00 (br, 2H, NH₂); 5.30 (br, H, NH); 5.45 (br, 1H,CH); 6.80 (d, 1H, Ar—H); 7.00-7.10 (m, 2H, Ar—H); 8.10 (s, 1H, PYR-H);1.213 wax-like; logp (HCOOH): 1.25; 1H-NMR (CDCl₃, 400 MHZ, δ in ppm):2.10 (m, 1H, 1H from CH₂); 2.35 (m, 1H, 1H from CH₂); 3.70 (s, 3H,OCH₃); 4.10 (m, 1H, 1H from CH₂O); 4.25 (m, 1H, 1H from CH₂O); 5.45 (br,1H, CH); 5.80 (br, 2H, NH₂); 6.00 (br, H, NH); 6.60 (s, 1H, Ar—H); 6.85(m, 2H, Ar—H); 8.00 (s, 1H, PYR-H); 1.215 wax-like; logp (HCOOH): 2.03;1H-NMR (CDCl₃, 400 MHZ, δ in ppm): 1.35 (s, 3H, CH₃); 1.40 (s, 3H, CH₃);2.00 (m, 1H, 1H from CH₂); 2.40 (m, 1H, 1H from CH₂); 5.00-5.10 (br, 3H,NH, NH₂); 5.55 (br, 1H, CH); 6.80 (d, 1H, Ar—H); 695 (d, 1H, Ar—H); 8.10(s, 1H, PYR-H); 1.216 wax-like; logp (HCOOH): 1.66; 1H-NMR (CDCl₃, 400MHZ, δ in ppm): 0.90 (d, 3H, CH₃); 2.60 (m, 1H, 1H from CH₂); 2.90 (m,1H, 1H from CH₂); 3.05 (dd, 1H, 1H from CH₂); 5.15 (br, 2H, NH₂); 5.25(br, H, NH); 5.80 (br, 1H, CH); 6.85-7.00 (m, 2H, Ar—H); 7.15 (m, 1H,Ar—H); 8.10 (s, 1H, PYR-H); 1.218 wax-like; logp (HCOOH): 1.60; 1H-NMR(CDCl₃, 400 MHZ, δ in ppm): 2.00 (m, 1H, 1H from CH₂); 2.65 (m, 1H, 1Hfrom CH₂); 2.90 (m, 1H, 1H from CH₂); 3.05 (dd, 1H, 1H from CH₂); 5.05(br, 2H, NH₂); 5.20 (br, H, NH); 5.75 (br, 1H, CH); 7.15-7.30 (m, 3H,Ar—H); 8.10 (s, 1H, PYR-H); 1.220 wax-like; logp (HCOOH): 1.48; 1H-NMR(CDCl₃, 400 MHZ, δ in ppm): 1.90 (m, 1H, 1H from CH₂); 2.30 (s, 3H,CH₃); 2.70 (m, 1H, 1H from CH₂); 2.85 (m, 1H, 1H from CH₂); 3.00 (m, 1H,1H from CH₂); 5.70-6.00 (m, 4H, NH₂, NH, CH); 7.05-7.30 (m, 3H, Ar—H);7.95 (s, 1H, PYR-H); 1.223 wax-like; logp (HCOOH): 1.78; 1H-NMR (CDCl₃,400 MHZ, δ in ppm): 1.20-2.10 (m, 14H); 2.50 (s, 3H, CH₃); 2.80 (m, 2H,2H from CH₂); 4.85 (m, 1H, 1H from CHO); 5.00 (br, 2H, NH₂); 5.50 (br,1H, CH); 7.05-7.30 (m, 4H, Ar—H); 8.70 (br, 1H, NH); 1.224 solid; logp(HCOOH): 3.83; 1.225 wax-like; logp (HCOOH): 3.83; 1H-NMR (CDCl₃, 400MHZ, δ in ppm): 1.80 (m, 3H, 3H from CH₂); 2.10 (m, 1H, 1H from CH₂);2.80 (m, 2H, 2H from CH₂); 3.90 (s, 3H, OCH₃); 4.80 (br, 2H, NH₂); 5.45(br, 1H, CH); 5.50 (br, 1H, NH); 7.05-7.30 (m, 4H, Ar—H); 1.225 solid,m.p.: 150-151° C.; logp (HCOOH): 0.83; 1.226 wax-like; logp (HCOOH):1.48; 1.256 wax-like; logp (HCOOH): 3.56; 1H-NMR (CDCl₃, 400 MHZ, δ inppm): 1.85 (m, 1H, 1H from CH₂); 2.65 (m, 1H, 1H from CH₂); 2.85 (m, 1H,1H from CH₂); 3.00 (m, 1H, 1H from CH₂); 3.90 (s, 3H, OCH₃); 4.80 (br,2H, NH₂); 5.60 (br, 1H, NH); 5.65 (br, 1H, CH); 7.15-7.35 (m, 4H, Ar—H);1.257 wax-like; logp (HCOOH): 3.90; 1H-NMR (CDCl₃, 400 MHZ, δ in ppm):1.15 (t, 3H, CH₃); 2.10 (m, 1H, 1H from CH₂); 2.20 (m, 1H, 1H from CH₂);2.55 (q, 2H, 2H from CH₂CH₃); 3.90 (s, 3H, OCH₃); 4.15 (m, 1H, 1H fromCH₂O); 4.25 (m, 1H, 1H from CH₂O); 4.85 (br, 2H, NH₂); 5.35 (br, 1H,CH); 5.55 (br, H, NH); 6.75 (d, 1H, Ar—H); 7.00 (d, 2H, Ar—H); 1.259wax-like; logp (HCOOH): 4.59; 1H-NMR (CDCl₃, 400 MHZ, δ in ppm): 1.20(d, 6H, 2 * CH₃); 1.85 (m, 1H, 1H from CH₂); 2.65 (m, 1H, 1H from CH₂);2.80-3.00 (m, 3H, 1H from CH (CH₃)₂, 2H from CH₂); 4.85 (br, 2H, NH₂);5.55 (br, H, NH); 5.70 (br, 1H, CH); 7.15-7.35 (m, 3H, Ar—H);

B. Formulation Examples

-   a) A dusting composition is obtained by mixing 10 parts by weight of    a compound of the formula (I) and/or salts thereof and 90 parts by    weight of talc as inert substance, and comminuting in a crushing    mill.-   b) A readily water-dispersible, wettable powder is obtained by    mixing 25 parts by weight of a compound of the formula (I) and/or    salts thereof, 64 parts by weight of kaolin-containing quartz as    inert substance, 10 parts by weight of potassium lignosulfonate and    1 part by weight of sodium oleoylmethyltaurate as wetting agent and    dispersant and grinding in a pin mill.-   c) A readily water-dispersible dispersion concentrate is obtained by    mixing 20 parts by weight of a compound of the formula (I) and/or    salts thereof with 6 parts by weight of alkylphenol polyglycol ether    (®Triton X 207), 3 parts by weight of isotridecanol polyglycol ether    (8 EO) and 71 parts by weight of paraffinic mineral oil (boiling    range e.g. ca. 255 to more than 277° C.) and grinding in an    attrition ball mill to a fineness below 5 microns.-   d) An emulsifiable concentrate is obtained from 15 parts by weight    of a compound of the formula (I) and/or salts thereof, 75 parts by    weight of cyclohexanone as solvent and 10 parts by weight of    oxethylated nonylphenol as emulsifier.-   e) Water-dispersible granules are obtained by mixing 75 parts by    weight of a compound of the formula (I) and/or salts thereof,    -   10 parts by weight of calcium lignosulfonate,    -   5 parts by weight of sodium lauryl sulfate,    -   3 parts by weight of polyvinyl alcohol and    -   7 parts by weight of kaolin,    -   grinding on a pin mill and granulating the powder in a fluidized        bed by spraying on water as granulation liquid.-   f) Water-dispersible granules are also obtained by homogenizing and    precomminuting    -   25 parts by weight of a compound of the formula (I) and/or salts        thereof,    -   5 parts by weight of sodium        2,2′-dinaphthylmethane-6,6′-disulfonate,    -   2 parts by weight of sodium oleoylmethyltaurate,    -   1 part by weight of polyvinyl alcohol,    -   17 parts by weight of calcium carbonate and    -   50 parts by weight of water    -   on a colloid mill, then grinding on a bead mill and atomizing        and drying the suspension obtained in this way in a spray tower        by means of a one-component nozzle.

C. Biological Examples Description of the Experiment 1. Pre-EmergenceHerbicidal Effect and Crop Plant Compatibility

Seeds of monocotyledonous or dicotyledonous weed plants or crop plantsare planted in wood-fiber pots in sandy loam and covered with earth. Thecompounds according to the invention, formulated in the form of wettablepowders (WP) or as emulsion concentrates (EC), are then applied asaqueous suspension or emulsion at a water application rate of 600 to 800I/ha (converted) with the addition of 0.2% of wetting agent to thesurface of the covering earth.

Following the treatment, the pots are placed in a greenhouse and keptunder good growth conditions for the test plants. The visual scoring ofthe damage on the test plants is carried out after an experiment time of3 weeks in comparison with untreated controls (herbicidal effect inpercent (%): 100% effect=plants have died, 0% effect=as control plants).

The following abbreviations are used in the tables below:

ABUTH: Abutilon theophrasti ALOMY: Alopecurus myosuroides AMARE:Amaranthus retroflexus CHEAL: Chenopodium album CYPES: Cyperusesculentus ECHCG: Echinochloa crus-galli LOLMU: Lolium multiflorumMATIN: Matricaria inodora POLCO: Polygonum convolvulus PHBPU: Pharbitispurpurea SETVI: Setaria viridis STEME: Stellaria media VERPE: Veronicapersica VIOTR: Viola tricolor

TABLE 1 Pre-emergence herbicidal effect Example No. Dosage ALOMY AMARECYPES ECHCG LOLMU MATIN POLCO SETVI STEME VERPE VIOTR 1.18 320 100 100100 1.17 320 100 100 1.31 320 100 100 80 100 100 1.27 320 100 100 80 100100 100 100 100 100 1.30 320 100 100 100 100 100 100 100 100 100 1001.35 320 80 100 80 100 100 90 100 100 1.42 320 100 100 100 100 100 100100 100 100 1.44 320 100 100 100 100

As the results show, the compounds according to the invention have agood herbicidal pre-emergence effectiveness in respect of a broadspectrum of weed grasses and weeds. For example, the compounds in table1 have very good herbicidal effect in respect of harmful plants such asStellaria media, Echinochloa crus-galli, Lolium multiflorum, Setariaviridis, Amaranthus retroflexus and Alopecurus myosuroides in thepre-emergence method at an application rate of 0.32 kg and less activesubstance per hectare.

2. Post-emergence herbicidal effect and crop plant compatibility Seedsof monocotyledonous or dicotyledonous weed plants or crop plants areplanted in wood-fiber pots in sandy loam, covered with earth and grownin a greenhouse under good growth conditions. 2 to 3 weeks after sowing,the test plants are treated in the one-leaf stage. The compoundsaccording to the invention, formulated in the form of wettable powders(WP) or as emulsion concentrates (EC), are then sprayed onto the greenplant parts as aqueous suspension or emulsion at a water applicationrate of 600 to 800 I/ha (converted) with the addition of 0.2% of wettingagent.

After ca. 3 weeks' standing time of the test plants in the greenhouseunder optimum growth conditions, the effect of the preparations isscored visually in comparison with untreated controls (herbicidal effectin percent (%): 100% effect=plants have died, 0% effect=as controlplants).

TABLE 2 Post-emergence herbicidal effect Ex- am- ple No. Dosage ABUTHAMARE CHEAL ECHCG LOLMU MATIN PHBPU POLCO SETVI STEME VERPE VIOTR 1.31320 90 100 80 90 90 1.27 320 90 100 85 85 80 80 85 85 1.30 320 85 95 8780 90 80 80 90 85 1.35 320 90 80 80 1.36 320 80 100 90 90 80 90 90 1.42320 100 90 100 80 80 80 90

As the results show, compounds according to the invention have goodherbicidal post-emergence effectiveness in respect of a broad spectrumof weed grasses and weeds. For example, the compounds in table 2 have avery good herbicidal effect towards harmful plants such as Echinochloacrus-galli, Abutilon theophrasti and Amaranthus retroflexus in thepost-emergence method at an application rate of 0.32 kg and less activesubstance per hectare.

1. A compound of the formula (I) and/or an agrochemically compatiblesalt thereof

in which R¹ and R², independently of one another, are selected from thegroup consisting of hydrogen, halogen, hydroxy, cyano, nitro, amino,C(O)OH, C(O)NH₂; (C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl,(C₁-C₆)-alkylcarbonyl, (C₁-C₆)-halo-alkylcarbonyl,(C₁-C₆)-alkylcarbonyloxy, (C₁-C₆)-haloalkylcarbonyloxy,(C₁-C₆)-alkylcarbonyl-(C₁-C₄)-alkyl; (C₁-C₆)-alkoxy, (C₁-C₆)-haloalkoxy,(C₁-C₆)-alkoxycarbonyl, (C₁-C₆)-haloalkoxycarbonyl,(C₁-C₆)-alkoxycarbonyl-(C₁-C₆)-alkyl,(C₁-C₆)-halo-alkoxycarbonyl-(C₁-C₆)-alkyl,(C₁-C₆)-alkoxycarbonyl-(C₁-C₆)-haloalkyl,(C₁-C₆)-haloalkoxycarbonyl-(C₁-C₆)-haloalkyl; (C₂-C₆)-alkenyl,(C₂-C₆)-haloalkenyl, (C₂-C₆)-alkenylcarbonyl,(C₂-C₆)-haloalkenylcarbonyl, (C₂-C₆)-alkenyloxy, (C₂-C₆)-haloalkenyloxy,(C₂-C₆)-alkenyloxycarbonyl, (C₂-C₆)-haloalkenyloxycarbonyl;(C₂-C₆)-alkynyl, (C₂-C₆)-haloalkynyl, (C₂-C₆)-alkynylcarbonyl,(C₂-C₆)-haloalkynylcarbonyl, (C₂-C₆)-alkynyloxy, (C₂-C₆)-haloalkynyloxy,(C₂-C₆)-alkynyloxycarbonyl, (C₂-C₆)-haloalkynyloxycarbonyl;tri(C₁-C₆)-alkylsilyl-(C₂-C₆)-alkynyl,di(C₁-C₆)-alkylsilyl-(C₂-C₆)-alkynyl,mono(C₁-C₆)-alkylsilyl-(C₂-C₆)-alkynyl, phenylsilyl-(C₂-C₆)-alkynyl;(C₆-C₁₄)-aryl, (C₆-C₁₄)-aryloxy, (C₆-C₁₄)-arylcarbonyl and(C₆-C₁₄)-aryl-oxycarbonyl, which may in each case be substituted on thearyl moiety by halogen, (C₁-C₆)-alkyl and/or (C₁-C₆)-haloalkyl;(C₆-C₁₄)-aryl-(C₁-C₆)-alkyl, (C₆-C₁₄)-aryl-(C₁-C₆)-alkoxy,(C₆-C₁₄)-aryl-(C₁-C₆)-alkylcarbonyl,(C₆-C₁₄)-aryl-(C₁-C₆)-alkylcarbonyloxy,(C₆-C₁₄)-aryl-(C₁-C₆)-alkoxycarbonyl,(C₆-C₁₄)-aryl-(C₁-C₆)-alkoxycarbonyloxy; mono((C₁-C₆)-alkyl)amino,mono((C₁-C₆)-haloalkyl)amino, di((C₁-C₆)-alkyl)amino,di((C₁-C₆)-haloalkyl)amino, ((C₁-C₆)-alkyl-(C₁-C₆)-haloalkyl)amino,N—((C₁-C₆)-alkanoyl)amino, N—((C₁-C₆)-haloalkanoyl)amino,aminocarbonyl-(C₁-C₆)-alkyl, di(C₁-C₆)-alkylaminocarbonyl-(C₁-C₆)-alkyl;mono((C₁-C₆)-alkyl)aminocarbonyl, mono((C₁-C₆)-haloalkyl)aminocarbonyl,di((C₁-C₆)-alkyl)aminocarbonyl, di((C₁-C₆)-haloalkyl)aminocarbonyl,di((C₁-C₆)-alkyl-(C₁-C₆)-haloalkyl)aminocarbonyl,N—((C₁-C₆)-alkanoyl)aminocarbonyl,N—((C₁-C₆)-haloalkanoyl)aminocarbonyl; (C₁-C₆)-alkoxy-(C₁-C₆)-alkyl,(C₁-C₆)-alkoxy-(C₁-C₆)-alkoxy, (C₁-C₆)-alk-oxycarbonyl-(C₁-C₆)-alkoxy;(C₃-C₈)-cycloalkyl, which may be optionally substituted on thecycloalkyl radical by (C₁-C₆)-alkyl and/or halogen; (C₃-C₈)-cycloalkoxy,(C₃-C₈)-cycloalkyl-C₁-C₆)-alkyl, (C₃-C₈)-cycloalkyl-(C₁-C₆)-haloalkyl,(C₃-C₈)-cycloalkyl-(C₁-C₆)-alkoxy,(C₃-C₈)-cycloalkyl-(C₁-C₆)-haloalkoxy, (C₃-C₈)-cycloalkylcarbonyl,(C₃-C₈)-cycloalkoxycarbonyl, (C₃-C₈)-cycloalkyl-(C₁-C₆)-alkylcarbonyl,(C₃-C₈)-cycloalkyl-(C₁-C₆)-haloalkylcarbonyl,(C₃-C₈)-cycloalkyl-(C₁-C₆)-alkoxycarbonyl,(C₃-C₈)-cycloalkyl-(C₁-C₆)-haloalkoxycarbonyl,(C₃-C₈)-cycloalkylcarbonyloxy, (C₃-C₈)-cycloalkoxycarbonyloxy,(C₃-C₈)-cycloalkyl-(C₁-C₆)-alkylcarbonyloxy,(C₃-C₈)-cycloalkyl-(C₁-C₆)-haloalkylcarbonyloxy,(C₃-C₈)-cycloalkyl-(C₁-C₆)-alkoxycarbonyloxy,(C₃-C₈)-cycloalkyl-(C₁-C₆)-haloalkoxy-carbonyloxy; (C₃-C₈)-cycloalkenyl,(C₃-C₈)-cycloalkenyloxy, (C₃-C₈)-cycloalkenyl-(C₁-C₆)-alkyl,(C₃-C₈)-cycloalkenyl-(C₁-C₆)-haloalkyl,(C₃-C₈)-cycloalkenyl-(C₁-C₆)-alkoxy,(C₃-C₈)-cycloalkenyl-(C₁-C₆)-haloalkoxy, (C₃-C₈)-cycloalkenylcarbonyl,(C₃-C₈)-cycloalkenyloxycarbonyl,(C₃-C₈)-cycloalkenyl-(C₁-C₆)-alkylcarbonyl,(C₃-C₈)-cycloalkenyl-(C₁-C₆)-haloalkylcarbonyl,(C₃-C₈)-cycloalkenyl-(C₁-C₆)-alkoxycarbonyl,(C₃-C₈)-cycloalkenyl-(C₁-C₆)-haloalkoxycarbonyl,(C₃-C₈)-cycloalkenylcarbonyloxy, (C₃-C₈)-cycloalkenyloxycarbonyloxy,(C₃-C₈)-cycloalkenyl-(C₁-C₆)-alkylcarbonyloxy,(C₃-C₈)-cycloalkenyl-(C₁-C₆)-haloalkylcarbonyloxy,(C₃-C₈)-cycloalkenyl-(C₁-C₆)-alkoxycarbonyloxy,(C₃-C₈)-cycloalkenyl-(C₁-C₆)-haloalkoxycarbonyloxy;hydroxy-(C₁-C₆)-alkyl, hydroxy-(C₁-C₆)-alkoxy, cyano-(C₁-C₆)-alkoxy,cyano-(C₁-C₆)-alkyl; (C₁-C₆)-alkylsulfonyl, (C₁-C₆)-alkylthio,(C₁-C₆)-alkylsulfinyl, (C₁-C₆)-haloalkylsulfonyl, (C₁-C₆)-haloalkylthio,(C₁-C₆)-haloalkylsulfinyl, (C₁-C₆)-alkylsulfonyl-(C₁-C₆)-alkyl,(C₁-C₆)-alkylthio-(C₁-C₆)-alkyl, (C₁-C₆)-alkylsulfinyl-(C₁-C₆)-alkyl,(C₁-C₆)-haloalkylsulfonyl-(C₁-C₆)-alkyl,(C₁-C₆)-haloalkylthio-(C₁-C₆)-alkyl,(C₁-C₆)-haloalkylsulfinyl-(C₁-C₆)-alkyl,(C₁-C₆)-alkylsulfonyl-(C₁-C₆)-haloalkyl,(C₁-C₆)-alkylthio-(C₁-C₆)-haloalkyl,(C₁-C₆)-alkylsulfinyl-(C₁-C₆)-haloalkyl,(C₁-C₆)-haloalkylsulfonyl-(C₁-C₆)-haloalkyl,(C₁-C₆)-haloalkylthio-(C₁-C₆)-haloalkyl,(C₁-C₆)-haloalkylsulfinyl-(C₁-C₆)-haloalkyl, (C₁-C₆)-alkylsulfonyloxy,(C₁-C₆)-haloalkylsulfonyloxy, (C₁-C₆)-alkylthiocarbonyl,(C₁-C₆)-haloalkylthiocarbonyl, (C₁-C₆)-alkylthiocarbonyloxy,(C₁-C₆)-haloalkylthiocarbonyloxy, (C₁-C₆)-alkylthio-(C₁-C₆)-alkyl,(C₁-C₆)-alkylthio-(C₁-C₆)-alkoxy,(C₁-C₆)-alkylthio-(C₁-C₆)-alkylcarbonyl,(C₁-C₆)-alkylthio-(C₁-C₆)-alkylcarbonyloxy, (C₄-C₁₄)-arylsulfonyl,(C₆-C₁₄)-arylthio, (C₆-C₁₄)-arylsulfinyl, (C₃-C₈)-cycloalkylthio,(C₃-C₈)-alkenylthio, (C₃-C₈)-cycloalkenylthio, (C₃-C₆)-alkynylthio; theradicals R¹ and R² together form a (C₂-C₆)-alkylene group, which maycomprise one or more oxygen and/or sulfur atoms, where the(C₂-C₆)-alkylene group may be mono- or polysubstituted by halogen andthe respective halogen substituents may be identical or different; R³ isselected from the group consisting of hydrogen, (C₁-C₆)-alkyl and(C₁-C₆)-haloalkyl; R⁴ and R⁵ in each case independently of one anotherare selected from the group consisting of hydrogen, (C₁-C₆)-alkyl,(C₁-C₆)-haloalkyl, hydroxy, (C₁-C₆)-alkoxy and (C₁-C₆)-haloalkoxy; or,together with the carbon atom to which they are bonded, form a three- toseven-membered ring; R⁶ and R⁷ in each case independently of one anotherare selected from the group consisting of hydrogen, (C₁-C₆)-alkyl,(C₁-C₆)-haloalkyl, (C₁-C₆)-alkoxy, (C₁-C₆)-haloalkoxy, (C₆-C₁₄)-aryl,(C₆-C₁₄)-aryloxy, (C₆-C₁₄)-arylcarbonyl and (C₆-C₁₄)-aryloxycarbonyl; orthe radicals R⁶ and R⁷ together form a (C₂-C₇)-alkylene group, which maycomprise one or more oxygen and/or sulfur atoms, where the(C₂-C₇)-alkylene group may be mono- or polysubstituted by halogen andthe respective halogen substituents may be identical or different, R⁸,R⁹, R¹⁰ and R¹¹, independently of one another, are in each case selectedfrom the group consisting of hydrogen, halogen, cyano, nitro,(C₁-C₆)-alkyl, (C₁-C₆)-alkylcarbonyl, (C₁-C₆)-alkyloxycarbonyl,(C₁-C₆)-alkylaminocarbonyl, (C₁-C₆)-dialkylaminocarbonyl,(C₁-C₆)-haloalkyl, (C₁-C₆)-alkoxy, (C₁-C₆)-haloalkoxy, (C₂-C₆)-alkynyl,(C₂-C₆)-haloalkynyl, (C₂-C₆)-alkynylcarbonyl,(C₂-C₆)-haloalkynylcarbonyl, (C₂-C₆)-alkynyloxy, (C₂-C₆)-haloalkynyloxy,(C₂-C₆)-alkynyloxycarbonyl and (C₂-C₆)-haloalkynyloxycarbonyl; and X isa bond, CH₂, O, S, carbonyl, NH, CR¹²R¹³ and/or NR¹⁴, R¹² and R¹³ ineach case independently of one another are selected from the groupconsisting of hydrogen, (C₁-C₆)-alkyl and (C₁-C₆)-haloalkyl, R¹⁴ isselected from the group consisting of hydrogen, (C₁-C₆)-alkyl, and(C₁-C₆)-haloalkyl, provided a) that at least one radical of R¹, R⁴, R⁵,R⁶, R⁷, R⁸, R⁹, R¹⁰ or R¹¹ is not hydrogen if R² is CF₃, b) R² does notdenote chloro if R¹ is NH₂.
 2. A compound of the formula (I) as claimedin claim 1, wherein the radical R¹ is selected from the group consistingof hydrogen, halogen, cyano, C(═O)NH₂, NO₂, (C₁-C₆)-alkyl,(C₁-C₆)-haloalkyl, (C₃-C₆)-cyclopropyl, (C₁-C₆)-alkoxy,(C₁-C₆)-thioalkyl, (C₁-C₆)-alkylthio, (C₂-C₆)-alkynyl,mono(C₁-C₆)-alkylamino, di(C₁-C₆)-alkylamino andtri(C₁-C₆)-alkylsilyl-(C₂-C₆)-alkynyl.
 3. A compound of the formula (I)as claimed in claim 1, wherein the radical R² is selected from the groupconsisting of hydrogen, halogen, (C₁-C₆)-alkylphenyl, (C₆-C₁₄)-aryl,which may be substituted on the aryl radical by (C₁-C₆)-alkyl,(C₆-C₁₄)-haloalkyl and/or halogen; C₆-aryl-(C₁-C₆)-haloalkyl,(C₁-C₆)-alkyl, (C₁-C₆)-haloalkyl, (C₁-C₆)-alkoxy,(C₁-C₆)-alkoxy-(C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl, which may besubstituted on the cycloalkyl radical by (C₁-C₆)-alkyl,(C₆-C₁₄)-haloaryl and/or halogen; 1-(C₁-C₆)-alkylcyclopropyl,1-((C₁-C₆)-alkyl-C₆-aryl)cyclopropyl, 1-(monohalophenyl)cyclopropyl,1-(dihalophenyl)cyclopropyl, mono(C₁-C₆)-alkylamino,di(C₁-C₆)-alkylamino, (C₁-C₆)-thioalkyl, (C₁-C₆)-alkylthio,(C₁-C₆)-alkoxy and amino.
 4. A compound of the formula (I) as claimed inclaim 1, wherein R¹ and R², together with the carbon atoms to which theyare bonded, form a five- or six-membered ring, which may be interruptedby one or two heteroatoms selected from the group consisting of oxygenand sulfur.
 5. A compound of the formula (I) as claimed in claim 1,wherein the radical R³ is hydrogen or (C₁-C₆)-alkyl.
 6. A compound ofthe formula (I) as claimed in claim 1, wherein the radicals R⁴ and R⁵,in each case independently of one another, are selected from the groupconsisting of hydrogen, (C₁-C₆)-alkyl, hydroxy, cyclopropyl and(C₁-C₆)-alkoxy.
 7. A compound of the formula (I) as claimed in claim 1,wherein the radicals R⁴ and R⁵ together form a (C₁-C₇)-alkylene groupwhich can comprise one or more oxygen and/or sulfur atoms, where the(C₁-C₇)-alkylene group may be mono- or polysubstituted by halogen andthe respective halogen substituents may be identical or different.
 8. Acompound of the formula (I) as claimed in claim 1, wherein the radicalsR⁶ and R⁷, independently of one another, are selected from the groupconsisting of hydrogen, (C₁-C₆)-alkyl and (C₆-C₁₄)-aryl.
 9. A compoundof the formula (I) as claimed in claim 1, wherein the radical R⁸ isselected from the group consisting of hydrogen, (C₁-C₆)-alkyl andhalogen.
 10. A compound of the formula (I) as claimed in claim 1,wherein the radical R⁹ is preferably selected from the group consistingof hydrogen and (C₁-C₆)-alkyl.
 11. A compound of the formula (I) asclaimed in claim 1, wherein the radical R¹⁰ is selected from the groupconsisting of hydrogen, (C₁-C₆)-alkyl, di(C₁-C₆)-alkylamino, halogen,(C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, (C₁-C₆)-alkyl-(C₂-C₆)-alkynyl,(C₁-C₆)-alkoxy-(C₁-C₆)-alkyl-(C₂-C₆)-alkynyl, cyano,(C₁-C₆)-alkoxycarbonyl and aminocarbonyl.
 12. A compound of the formula(I) as claimed in claim 1, wherein R¹¹ is selected from the groupconsisting of hydrogen and (C₁-C₆)-alkyl.
 13. A compound of the formula(I) as claimed in claim 1, wherein X is selected from the groupconsisting of CH₂, O and a chemical bond.
 14. A process for thepreparation of compounds of the formula (I) of claim 1

which comprises (1) reacting a compound of the formula (II)

in which Z¹ is an exchangeable radical or a leaving group, with an amineof the formula (III) or an acid addition salt thereof.


15. A herbicidal or plant growth regulating composition, which comprisesone or more compounds of the formula (I) or salts thereof as claimed inclaim
 1. 16. A method for controlling harmful plants or for regulatingthe growth of plants, which comprises applying an effective amount ofone or more compounds of the formula (I) or salts thereof as claimed inclaim 1 to plants, plant parts, plant seeds or to an area undercultivation.